6576-51-8

Basic information

• Product Name: distamycin A hydrochloride from*streptomyces dist
• Synonyms: Stallimycin hydrochloride [USAN]; Stallimycin hydrochloride; 1H-Pyrrole-2-carboxamide, N-(5-(((3-amino-3-iminopropyl)amino)carbonyl)-1-methyl-1H-pyrrol-3-yl)-4-(((4-(formylamino)-1-methyl-1H-pyrrol-2-yl)carbonyl)amino)-1-methyl-, monohydrochloride; Distamycin A hydrochloride; Estalimicina clorhidrato; Estalimicina clorhidrato [Spanish]; F.I. 6426; FI 6426; Herperal; N''-(2-Amidinoethyl)-4-formamido-1,1',1''-trimethyl-N,4':N',4''-ter(pyrrole-2-carboxamide) monohydrochloride; N'-(2-Amidinoethyl)-4-formamido-1,1',1'-trimethyl-N,4':N',4'-ter(pyrrole-2-carboxamide) monohydrochloride; NSC 150528; Stallimycin HCl; (N,4':N',4''-Terpyrrole)-2-carboxamide, N''-(2-amidinoethyl)-4-formamido-1,1',1''-trimethyl-, hydrochloride; N-(5-(((3-Amino-3-iminopropyl)amino)carbonyl)-1-methyl-1H-pyrrol-3-yl)-4-(((4-(formylamino)-1-methyl-1H-pyrrol-2-yl)carbonyl)amino)-1-methyl-1H-pyrrole-2-carboxamide monohydrochloride; hydrogen chloride N-{5-[(5-{[(3Z)-3-amino-3-iminopropyl]carbamoyl}-1-methyl-1H-pyrrol-3-yl)carbamoyl]-1-methyl-1H-p
• CAS NO: 6576-51-8
• Molecular Formula: C₂₂H₂₇N₉O₄*ClH
• Molecular Weight: 517.9686
• EINECS: 229-505-6
• Mol File: 6576-51-8.mol
• Article Data: 2

Chemical Properties

• Melting Point: 184-187° (Arcamone, 1967). Also reported as 189-193° from ethanol-ethyl acetate (Bialer)
• Boiling Point: 715.4°C at 760 mmHg
• Flash Point: 386.4°C
• Vapor Pressure: 9.91E-21mmHg at 25°C
• Storage Temp.: ?20°C
• CAS DataBase Reference: distamycin A hydrochloride from*streptomyces dist(CAS DataBase Reference)
• NIST Chemistry Reference: distamycin A hydrochloride from*streptomyces dist(6576-51-8)
• EPA Substance Registry System: distamycin A hydrochloride from*streptomyces dist(6576-51-8)

Safety Data

• Hazard Codes: Xi
• Statements: 43
• Safety Statements: 36/37
• WGK Germany: 3
• RTECS: WZ7110000
• Hazardous Substances Data: 6576-51-8(Hazardous Substances Data)

Usage

Therapeutic Function

Antibiotic

Synthetic route

N-Succinimidyl 4-<<<4-<<<4-(Formylamino)-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrole-2-carboxylate (77727-43-6) + (1-amino-3-ammoniopropylidene)ammonium dihydrobromide (77152-88-6) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
With hydrogenchloride; sodium hydrogencarbonate In 1,4-dioxane; water 1.) 15 min, ice-cooled, 2.) room temperature, overnight; Yield given;

1-methyl-4-<1-methyl-4-(1-methyl-4-aminopyrrole-2-carboxamido)pyrrole-2-carboxamido>pyrrole-2-carboxamidopropionamidine hydrochloride (3786-88-7) + N-formylimidazole (3197-61-3) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
In tetrahydrofuran; methanol at -40℃; for 0.5h; Yield given;

1-Methyl-2-pyrrolecarboxylic acid (6973-60-0) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 8 steps 1: 43 percent / 1.) 70percent nitric acid, acetic anhydride / 1.) a) -15 deg C, 0.5 h, b) RT, 20 min 2: SOCl2 / tetrahydrofuran / 0.08 h / Heating 3: Hunig's base / tetrahydrofuran / -20 - 20 °C 4: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C 5: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 6: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 7: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 8: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme
Multi-step reaction with 8 steps 1: 43 percent / 1.) 70percent nitric acid, acetic anhydride / 1.) a) -15 deg C, 0.5 h, b) RT, 20 min 2: SOCl2 / tetrahydrofuran / 0.08 h / Heating 3: 1.) H2, 2.) Hunig's base / 10percent Pd/C / 1.) MeOH, 1 atm, 2.) THF, 3) THF, RT, 30 min 4: 95 percent / NaOH / H2O; ethanol / Heating 5: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 6: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 7: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 8: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

1-methyl-4-nitro-pyrrol-2-carboxylic acid (13138-78-8) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 7 steps 1: SOCl2 / tetrahydrofuran / 0.08 h / Heating 2: Hunig's base / tetrahydrofuran / -20 - 20 °C 3: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C 4: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 5: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 6: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 7: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme
Multi-step reaction with 7 steps 1: SOCl2 / tetrahydrofuran / 0.08 h / Heating 2: 1.) H2, 2.) Hunig's base / 10percent Pd/C / 1.) MeOH, 1 atm, 2.) THF, 3) THF, RT, 30 min 3: 95 percent / NaOH / H2O; ethanol / Heating 4: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 5: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 6: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 7: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme
Multi-step reaction with 8 steps 1: H2, 1.0 M Na2CO3(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature 2: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature 3: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C 4: TFA / CH2Cl2 5: EDC / dimethylformamide / 40 °C 6: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 7: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 8: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme

1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxylic acid (97950-76-0) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 2: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 3: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 4: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

methyl 1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carbonate (69910-20-9) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: 95 percent / NaOH / H2O; ethanol / Heating 2: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 3: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 4: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 5: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

1-methyl-4-nitro-1H-pyrrole-2-carbonyl chloride (28494-51-1) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 6 steps 1: Hunig's base / tetrahydrofuran / -20 - 20 °C 2: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C 3: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 4: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 5: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 6: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme
Multi-step reaction with 6 steps 1: 1.) H2, 2.) Hunig's base / 10percent Pd/C / 1.) MeOH, 1 atm, 2.) THF, 3) THF, RT, 30 min 2: 95 percent / NaOH / H2O; ethanol / Heating 3: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 4: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 5: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 6: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

1-methyl-4-nitropyrrole-2-carboxylic acid methyl ester (13138-76-6) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 8 steps 1: 92 percent / aq. NaOH / Heating 2: SOCl2 / tetrahydrofuran / 0.08 h / Heating 3: Hunig's base / tetrahydrofuran / -20 - 20 °C 4: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C 5: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 6: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 7: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 8: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme
Multi-step reaction with 8 steps 1: 92 percent / aq. NaOH / Heating 2: SOCl2 / tetrahydrofuran / 0.08 h / Heating 3: 1.) H2, 2.) Hunig's base / 10percent Pd/C / 1.) MeOH, 1 atm, 2.) THF, 3) THF, RT, 30 min 4: 95 percent / NaOH / H2O; ethanol / Heating 5: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 6: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 7: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 8: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

1-methyl-4-nitro-1H-pyrrole-2-carboxylic acid (2-cyanoethyl)amide (3185-95-3) → distamycin A hydrochloride (6576-51-8)

Conditions

Yield

Multi-step reaction with 5 steps 1: 1.) H2, 2.) HCl / 10percent Pd/C / 1.) methanol, 40 deg C, 1 atm, 2.) isopropanol, -30 deg C 2: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 3: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 4: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 5: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

3-<1-methyl-4-<1-methyl-4-(1-methyl-4-nitropyrrole-2-carboxamido)pyrrole-2-carboxamido>pyrrole-2-carboxamido>propionitrile (2522-28-3) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 2: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 3: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

N-(3-amino-3-iminopropyl)-1-methyl-4-{[(1-methyl-4-{[(1-methyl-4-nitro-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrol-2-yl)carbonyl]amino}-1H-pyrrole-2-carboxamide hydrochloride (6576-50-7) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 2: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

1-methyl-4-aminopyrrole-2-carboxamidopropionitrile hydrochloride → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: 64 percent / 1,8-bis(dimethylamino)naphthalene, dicyclohexylcarbodiimide / tetrahydrofuran; dimethylformamide / 3 h / Ambient temperature 2: 1.) HCl, 2.) NH3 / 1.) EtOH, RT, 1.5 h, 2.) EtOH, 1 h, RT 3: 70 percent / H2 / 10percent Pd/C / methanol / 40 °C 4: methanol; tetrahydrofuran / 0.5 h / -40 °C View Scheme

4-amino-1-methylpyrrole-2-carboxylic acid (45776-13-4) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 7 steps 1: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature 2: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C 3: TFA / CH2Cl2 4: EDC / dimethylformamide / 40 °C 5: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 6: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 7: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme
Multi-step reaction with 10 steps 1: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature 2: Cs2CO3 / ethanol; H2O 3: dimethylformamide / 40 °C 4: TFA / CH2Cl2 / 1 h / Ambient temperature; stoppered flask 5: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C 6: TFA / CH2Cl2 7: EDC / dimethylformamide / 40 °C 8: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 9: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 10: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme
Multi-step reaction with 10 steps 1: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature 2: Cs2CO3 / ethanol; H2O 3: dimethylformamide / 40 °C 4: TFA / CH2Cl2 / 1 h / Ambient temperature; stoppered flask 5: tetramethylguanidine / dimethylsulfoxide / 20 h / 50 °C 6: TFA / CH2Cl2 7: EDC / dimethylformamide / 40 °C 8: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 9: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 10: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme
Multi-step reaction with 8 steps 1: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature 2: 71 percent / N,N'-dicyclohexylcarbodiimide / dimethylformamide / 20 h / Ambient temperature 3: tetramethylguanidine / dimethylsulfoxide / 20 h / 50 °C 4: TFA / CH2Cl2 5: EDC / dimethylformamide / 40 °C 6: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 7: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 8: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme
Multi-step reaction with 5 steps 1: 2.5 h / ice-bath 2: EDC / dimethylformamide / 40 °C 3: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 4: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 5: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme

ethyl 1-methyl-4-nitro-1H-pyrrole-2-carboxylate (2853-29-4) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 9 steps 1: 69 percent / 2 M NaOH / ethanol / 1.5 h / Heating 2: H2, 1.0 M Na2CO3(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature 3: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature 4: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C 5: TFA / CH2Cl2 6: EDC / dimethylformamide / 40 °C 7: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 8: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 9: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme
Multi-step reaction with 12 steps 1: 69 percent / 2 M NaOH / ethanol / 1.5 h / Heating 2: H2, 1.0 M Na2CO3(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature 3: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature 4: Cs2CO3 / ethanol; H2O 5: dimethylformamide / 40 °C 6: TFA / CH2Cl2 / 1 h / Ambient temperature; stoppered flask 7: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C 8: TFA / CH2Cl2 9: EDC / dimethylformamide / 40 °C 10: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 11: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 12: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme
Multi-step reaction with 12 steps 1: 69 percent / 2 M NaOH / ethanol / 1.5 h / Heating 2: H2, 1.0 M Na2CO3(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature 3: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature 4: Cs2CO3 / ethanol; H2O 5: dimethylformamide / 40 °C 6: TFA / CH2Cl2 / 1 h / Ambient temperature; stoppered flask 7: tetramethylguanidine / dimethylsulfoxide / 20 h / 50 °C 8: TFA / CH2Cl2 9: EDC / dimethylformamide / 40 °C 10: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 11: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 12: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme
Multi-step reaction with 10 steps 1: 69 percent / 2 M NaOH / ethanol / 1.5 h / Heating 2: H2, 1.0 M Na2CO3(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature 3: tetrahydrofuran; diethyl ether / 1.) 1 h, ice cooled, 2.) 2 h, ambient temperature 4: 71 percent / N,N'-dicyclohexylcarbodiimide / dimethylformamide / 20 h / Ambient temperature 5: tetramethylguanidine / dimethylsulfoxide / 20 h / 50 °C 6: TFA / CH2Cl2 7: EDC / dimethylformamide / 40 °C 8: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 9: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 10: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme
Multi-step reaction with 7 steps 1: 69 percent / 2 M NaOH / ethanol / 1.5 h / Heating 2: H2, 1.0 M Na2CO3(aq.) / 5percent Pd/C / 3.5 h / 3102.9 Torr / Ambient temperature 3: 2.5 h / ice-bath 4: EDC / dimethylformamide / 40 °C 5: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 6: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 7: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme

Benzyl 4-Amino-1-methylpyrrole-2-carboxylate (77716-14-4) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 6 steps 1: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C 2: TFA / CH2Cl2 3: EDC / dimethylformamide / 40 °C 4: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 5: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 6: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme
Multi-step reaction with 6 steps 1: tetramethylguanidine / dimethylsulfoxide / 20 h / 50 °C 2: TFA / CH2Cl2 3: EDC / dimethylformamide / 40 °C 4: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 5: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 6: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme

Benzyl 4-<<(4-Amino-1-methylpyrrol-2-yl)carbonyl>amino>-1-methylpyrrole-2-carboxylate (77716-19-9) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: EDC / dimethylformamide / 40 °C 2: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 3: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 4: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme

4-formamido-1-methylimidazole-2-carboxylic acid (77716-18-8) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: EDC / dimethylformamide / 40 °C 2: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 3: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 4: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme

4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acid (77716-11-1) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 6 steps 1: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C 2: TFA / CH2Cl2 3: EDC / dimethylformamide / 40 °C 4: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 5: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 6: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme
Multi-step reaction with 9 steps 1: Cs2CO3 / ethanol; H2O 2: dimethylformamide / 40 °C 3: TFA / CH2Cl2 / 1 h / Ambient temperature; stoppered flask 4: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C 5: TFA / CH2Cl2 6: EDC / dimethylformamide / 40 °C 7: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 8: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 9: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme
Multi-step reaction with 9 steps 1: Cs2CO3 / ethanol; H2O 2: dimethylformamide / 40 °C 3: TFA / CH2Cl2 / 1 h / Ambient temperature; stoppered flask 4: tetramethylguanidine / dimethylsulfoxide / 20 h / 50 °C 5: TFA / CH2Cl2 6: EDC / dimethylformamide / 40 °C 7: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 8: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 9: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme
Multi-step reaction with 7 steps 1: 71 percent / N,N'-dicyclohexylcarbodiimide / dimethylformamide / 20 h / Ambient temperature 2: tetramethylguanidine / dimethylsulfoxide / 20 h / 50 °C 3: TFA / CH2Cl2 4: EDC / dimethylformamide / 40 °C 5: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 6: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 7: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme

benzyl 4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrole-2-carboxylate (77716-13-3) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 7 steps 1: TFA / CH2Cl2 / 1 h / Ambient temperature; stoppered flask 2: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C 3: TFA / CH2Cl2 4: EDC / dimethylformamide / 40 °C 5: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 6: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 7: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme
Multi-step reaction with 7 steps 1: TFA / CH2Cl2 / 1 h / Ambient temperature; stoppered flask 2: tetramethylguanidine / dimethylsulfoxide / 20 h / 50 °C 3: TFA / CH2Cl2 4: EDC / dimethylformamide / 40 °C 5: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 6: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 7: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme

4-tert-butoxycarbonylamino-1-methyl-1H-pyrrole-2-carboxylic acid benzotriazol-1yl ester (77716-16-6) → distamycin A hydrochloride (6576-51-8)

Conditions

Yield

Multi-step reaction with 6 steps 1: tetramethylguanidine / dimethylsulfoxide / 20 h / 50 °C 2: TFA / CH2Cl2 3: EDC / dimethylformamide / 40 °C 4: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 5: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 6: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme

benzyl 4-<<<4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrol-2-yl>carbonyl>amino>-1-methyl-pyrrole-2-carboxylate (77716-15-5) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 5 steps 1: TFA / CH2Cl2 2: EDC / dimethylformamide / 40 °C 3: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 4: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 5: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme

4-(4-(4-formamido-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylic acid (77716-21-3) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 2: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme

Benzyl 4-<<<4-<<<4-(Formylamino)-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrole-2-carboxylate (77716-20-2) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 2: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 3: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme

Caesium; 4-tert-butoxycarbonylamino-1-methyl-1H-pyrrole-2-carboxylate (77716-12-2) → distamycin A hydrochloride (6576-51-8)

Conditions	Yield
Multi-step reaction with 8 steps 1: dimethylformamide / 40 °C 2: TFA / CH2Cl2 / 1 h / Ambient temperature; stoppered flask 3: 1-ethyl-3-<3-(dimethylamino)propyl>carbodiimide hydrochloride / dimethylformamide / 40 °C 4: TFA / CH2Cl2 5: EDC / dimethylformamide / 40 °C 6: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 7: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 8: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme
Multi-step reaction with 8 steps 1: dimethylformamide / 40 °C 2: TFA / CH2Cl2 / 1 h / Ambient temperature; stoppered flask 3: tetramethylguanidine / dimethylsulfoxide / 20 h / 50 °C 4: TFA / CH2Cl2 5: EDC / dimethylformamide / 40 °C 6: H2 / 5percent Pd/C / dimethylformamide / 2 h / 3102.9 Torr / Ambient temperature 7: 88 percent / DCC / dimethylformamide / 1.) 70 min, 0 deg C, 2.) 40 deg C, overnight 8: 1.) NaHCO3, 2.) HCl / H2O; dioxane / 1.) 15 min, ice-cooled, 2.) room temperature, overnight View Scheme

distamycin A hydrochloride (6576-51-8) → 3-{[4-({4-[(4-amino-1-methyl-1H-pyrrole-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carbonyl}-amino)-1-methyl-1H-pyrrole-2-carbonyl]-amino}-propionic acid

Conditions	Yield
With sodium hydroxide In methanol for 24h; Heating;	100%

distamycin A hydrochloride (6576-51-8) + ethylenediamine (107-15-3) → N-[5-({[5-({[2-(4,5-dihydro-1H-imidazol-2-yl)ethyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide hydrochloride

Conditions	Yield
In methanol at 20℃; for 24h;	95%

CYANAMID (420-04-2) + distamycin A hydrochloride (6576-51-8) → N-[5-({[5-({[3-amino-3-(cyanoimino)propyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide (194483-83-5)

Conditions	Yield
Stage #1: CYANAMID With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Stage #2: distamycin A hydrochloride In N,N-dimethyl-formamide for 2h;	93%
Stage #1: CYANAMID With sodium hydride In N,N-dimethyl-formamide for 0.5h; Stage #2: distamycin A hydrochloride In N,N-dimethyl-formamide for 5h;	92%
Stage #1: CYANAMID With sodium hydride In DMF (N,N-dimethyl-formamide) at 20℃; for 0.5h; Stage #2: distamycin A hydrochloride In DMF (N,N-dimethyl-formamide) at 20℃; for 2h; Stage #3: With acetic acid In DMF (N,N-dimethyl-formamide) pH=7;

CYANAMID (420-04-2) + distamycin A hydrochloride (6576-51-8) → N-[5-({[5-({[3-amino-3-(cyanoimino)propyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide hydrochloride

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 5.5h;	92%

distamycin A hydrochloride (6576-51-8) → N-(5-{[(5-{[(2-cyanoethyl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide (71084-59-8)

Conditions	Yield
With sodium carbonate In N,N-dimethyl-formamide at 70℃; for 3h;	87%
With succinic acid anhydride; sodium carbonate In N,N-dimethyl-formamide at 70℃; for 3h;	87%
With succinic acid anhydride; potassium carbonate In N,N-dimethyl-formamide for 3h; Ambient temperature;	75%

distamycin A hydrochloride (6576-51-8) → 4-amino-N-[5-({5-[(3-amino-3-oxopropyl)carbamoyl]-1-methyl-1H-pyrrol-3-yl}carbamoyl)-1-methyl-1H-pyrrol-3-yl]-1-methyl-1H-pyrrole-2-carboxamide

Conditions	Yield
With sodium hydroxide In methanol at 60℃; for 4h;	75%

distamycin A hydrochloride (6576-51-8) + methylamine (74-89-5) → N-[5-({[5-({[3-imino-3-(methylamino)propyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide dihydrochloride

Conditions	Yield
In water; N,N-dimethyl-formamide at 20℃; for 29h;	73%

methylamine hydrochloride (593-51-1) + distamycin A hydrochloride (6576-51-8) → N-[5-({[5-({[3-amino-3-(methylimino)propyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide hydrochloride

Conditions	Yield
In water; N,N-dimethyl-formamide at 20℃; for 12h;	73%
In DMF (N,N-dimethyl-formamide) for 8h;

distamycin A hydrochloride (6576-51-8) + methylamine (74-89-5) → N-[5-({[5-({[3-amino-3-(N-methylcarbamoyl)ethyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide (863319-29-3) + N-[5-({[5-({[2-(carbamoyl)ethyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide (17165-05-8)

Conditions	Yield
With water In N,N-dimethyl-formamide at 80℃; for 3h;	A 18% B 57%

distamycin A hydrochloride (6576-51-8) → N-[5-({[5-({[3-amino-3-(hydroxyimino)propyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide (203258-75-7)

Conditions	Yield
With hydroxylamine In N,N-dimethyl-formamide at 70℃; for 2h;	52%
With TEA; hydroxylamine hydrochloride In N,N-dimethyl-formamide at 70℃; for 1h;	52%

distamycin A hydrochloride (6576-51-8) + methylamine (74-89-5) → 4-formylamino-1-methyl-N-[1-methyl-5-({[1-methyl-5-({[3-(methylamino)-3-(methylimino)propyl]amino}carbonyl)-1H-pyrrol-3-yl]amino}carbonyl)-1H-pyrrol-3-yl]-1H-pyrrole-2-carboxamide hydrochloride

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 6h;	42%

distamycin A hydrochloride (6576-51-8) + methylamine (74-89-5) → 4-(formylamino)-1-methyl-N-[1-methyl-5-({[1-methyl-5-({[3-(methylamino)-3-(methylimino)propyl]amino}carbonyl)-1H-pyrrol-3-yl]amino}carbonyl)-1H-pyrrol-3-yl]-1H-pyrrole-2-carboxamide dihydrochloride

Conditions	Yield
In water; N,N-dimethyl-formamide at 80℃; for 3h;	32%

distamycin A hydrochloride (6576-51-8) + dimethyl amine (124-40-3) → N-[5-({[5-({[3-(dimethylamino)-3-iminopropyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide hydrochloride

Conditions	Yield
In N,N-dimethyl-formamide at 20℃; for 72h;	20%

glutaric anhydride, (108-55-4) + distamycin A hydrochloride (6576-51-8) → 4-(3-{[4-({4-[(4-Formylamino-1-methyl-1H-pyrrole-2-carbonyl)-amino]-1-methyl-1H-pyrrole-2-carbonyl}-amino)-1-methyl-1H-pyrrole-2-carbonyl]-amino}-1-imino-propylcarbamoyl)-butyric acid

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Ambient temperature;

acetic anhydride (108-24-7) + distamycin A hydrochloride (6576-51-8) → C24H29N9O5

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide Ambient temperature;

CYANAMID (420-04-2) + distamycin A hydrochloride (6576-51-8) → C23H26N10O4 (194483-83-5)

Conditions	Yield
With base In N,N-dimethyl-formamide at 70℃; Substitution;

distamycin A hydrochloride (6576-51-8) → N-[5-({[5-({[2-(carbamoyl)ethyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide (17165-05-8)

Conditions	Yield
With sodium hydroxide In acetonitrile at 70℃; Hydrolysis;

distamycin A hydrochloride (6576-51-8) → C22H27N9O5 (203258-75-7)

Conditions	Yield
With hydroxylamine In N,N-dimethyl-formamide at 70℃; Substitution;

distamycin A hydrochloride (6576-51-8) + dimethyl amine (124-40-3) → C24H31N9O4 (85407-13-2)

Conditions	Yield
With base In N,N-dimethyl-formamide at 70℃; Substitution;

distamycin A hydrochloride (6576-51-8) + ethylenediamine (107-15-3) → C24H29N9O4 (107580-76-7)

Conditions	Yield
With base In N,N-dimethyl-formamide at 70℃; Substitution;

distamycin A hydrochloride (6576-51-8) + methylamine (74-89-5) → C23H29N9O4 (85407-11-0)

Conditions	Yield
With base In N,N-dimethyl-formamide at 70℃; Substitution;

distamycin A hydrochloride (6576-51-8) + methylamine (74-89-5) → C24H31N9O4 (755734-70-4)

Conditions	Yield
With base In N,N-dimethyl-formamide at 70℃; Substitution;

distamycin A hydrochloride (6576-51-8) → 4-amino-N-(5-{[(5-{[(3-amino-3-iminopropyl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)-1-methyl-1H-pyrrole-2-carboxamide dihydrochloride (17165-10-5)

Conditions	Yield
With hydrogenchloride In methanol at 20℃; for 24h;

distamycin A hydrochloride (6576-51-8) → N-[5-({[5-({[2-(carbamoyl)ethyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-[N,N-bis(oxiranylmethyl)amino]-1-methyl-1H-pyrrole-2-carboxamide

Conditions	Yield
Multi-step reaction with 3 steps 1: 57 percent / H2O / dimethylformamide / 3 h / 80 °C 2: aq. HCl / aq. ethanol / 24 h / 20 °C 3: TEA / dimethylformamide / 3 h / 20 °C View Scheme

distamycin A hydrochloride (6576-51-8) → N-[5-({[5-({[2-(methylcarbamoyl)ethyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-[N,N-bis(oxiranylmethyl)amino]-1-methyl-1H-pyrrole-2-carboxamide

Conditions	Yield
Multi-step reaction with 3 steps 1: 18 percent / H2O / dimethylformamide / 3 h / 80 °C 2: aq. HCl / aq. ethanol / 24 h / 20 °C 3: TEA / dimethylformamide / 3 h / 20 °C View Scheme

distamycin A hydrochloride (6576-51-8) → N-[5-({[5-({[3-amino-3-(hydroxyimino)propyl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]amino}carbonyl)-1-methyl-1H-pyrrol-3-yl]-4-[N,N-bis(oxiranylmethyl)amino]-1-methyl-1H-pyrrole-2-carboxamide

Conditions	Yield
Multi-step reaction with 3 steps 1: 52 percent / NH2OH*HCl; TEA / dimethylformamide / 1 h / 70 °C 2: aq. HCl / aq. ethanol / 24 h / 20 °C 3: TEA / dimethylformamide / 3 h / 20 °C View Scheme

Upstream product

• 77727-43-6 N-Succinimidyl 4-<<<4-<<<4-(Formylamino)-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrole-2-carboxylate 
• 77152-88-6 (1-amino-3-ammoniopropylidene)ammonium dihydrobromide 
• 13138-78-8 1-methyl-4-nitro-pyrrol-2-carboxylic acid 
• 28494-51-1 1-methyl-4-nitro-1H-pyrrole-2-carbonyl chloride 
• 13138-76-6 1-methyl-4-nitropyrrole-2-carboxylic acid methyl ester 
• 77716-12-2 Caesium; 4-tert-butoxycarbonylamino-1-methyl-1H-pyrrole-2-carboxylate 
• 77716-20-2 Benzyl 4-<<<4-<<<4-(Formylamino)-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrol-2-yl>carbonyl>amino>-1-methylpyrrole-2-carboxylate 
• 77716-21-3 4-(4-(4-formamido-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxamido)-1-methyl-1H-pyrrole-2-carboxylic acid 
• 77716-15-5 benzyl 4-<<<4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrol-2-yl>carbonyl>amino>-1-methyl-pyrrole-2-carboxylate 
• 77716-16-6 4-tert-butoxycarbonylamino-1-methyl-1H-pyrrole-2-carboxylic acid benzotriazol-1yl ester 
• 77716-13-3 benzyl 4-<<(tert-butyloxy)carbonyl>amino>-1-methyl-pyrrole-2-carboxylate 
• 77716-11-1 4-[(tert-butoxycarbonyl)amino]-1-methyl-1H-pyrrole-2-carboxylic acid 
• 77716-18-8 4-formamido-1-methylimidazole-2-carboxylic acid 
• 77716-19-9 Benzyl 4-<<(4-Amino-1-methylpyrrol-2-yl)carbonyl>amino>-1-methylpyrrole-2-carboxylate 

Downstream Products

• 71084-59-8 N-(5-{[(5-{[(2-cyanoethyl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)amino]carbonyl}-1-methyl-1H-pyrrol-3-yl)-4-(formylamino)-1-methyl-1H-pyrrole-2-carboxamide 
• 85407-11-0 C₂₃H₂₉N₉O₄ 
• 85407-13-2 C₂₄H₃₁N₉O₄ 

Relevant articles and documents

Efficient Total Syntheses of the Oligopeptide Antibiotics Netropsin and Distamycin

New and efficient total syntheses of the natural oligopeptide antiviral antibiotics netropsin and distamycin are described.These procedures feature a different strategy of introduction of the terminal groups from that used hitherto, high yield coupling steps, improvements in the Pinner reaction for introducing the amidine moiety, and the novel use of N-formylimidazole for introduction of the formyl moiety in distamycin.The methods also avoid column chromatography with the attendant contamination of the oligopeptide hydrochlorides with inorganic salts eluted from adsorbents.The synthetic procedures are general and may be adapted to the synthesis of related oligopeptide structures.