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CAS No.: | 123663-49-0 |
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Name: | Iguratimod |
Article Data: | 5 |
Molecular Structure: | |
Formula: | C17H14N2O6S |
Molecular Weight: | 374.374 |
Synonyms: | T 614;T614 (antiinflammatory);Ailamode;3-Formylamino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one;N-[3-(Formylamino)-4-oxo-6-phenoxy-4H-chromen-7-yl]methanesulfonamide; |
EINECS: | 808-127-0 |
Density: | 1.52 g/cm3 |
Melting Point: | 238.0 to 242.0 °C |
Boiling Point: | 580.6 °C at 760 mmHg |
Flash Point: | 304.9 °C |
Appearance: | white powder |
PSA: | 123.09000 |
LogP: | 4.38780 |
N,N-dimethyl-formamide dimethyl acetal
α-formamido-2'-hydroxy-4'-methanesulfonamido-5'-phenoxyacetophenone
Iguratimod
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 15℃; for 8h; Cyclization; | 87% |
Acetic formic anhydride
N-(3-amino-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl)methanesulfonamide
Iguratimod
Conditions | Yield |
---|---|
In dichloromethane at 20℃; for 1h; Formylation; | 73% |
N-(3-amino-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl)methanesulfonamide
Iguratimod
Conditions | Yield |
---|---|
With formic acid; acetic anhydride In dichloromethane; di-isopropyl ether | 73% |
4-methoxy-2-nitro-1-phenoxybenzene
Iguratimod
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C 2: 82 percent / pyridine / 1 h / 20 °C 3: 90 percent / AlCl3; HCl / nitrobenzene / 10 h / 25 - 30 °C 4: 91 percent / acetone / 3 h 5: 95 percent / NaI; AlCl3 / acetonitrile / 3 h / 20 °C 6: 87 percent / dimethylformamide / 8 h / 15 °C View Scheme | |
Multi-step reaction with 9 steps 1: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C 2: 82 percent / pyridine / 1 h / 20 °C 3: 84 percent / aluminum chloride / CH2Cl2 / 1 h / 15 - 20 °C 4: 70 percent aq. HClO4 / 1 h / 20 °C 5: H2O / 0.08 h / Heating 6: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr 7: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C 8: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C 9: 73 percent / CH2Cl2 / 1 h / 20 °C View Scheme |
5-methoxy-2-phenoxyaniline
Iguratimod
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 82 percent / pyridine / 1 h / 20 °C 2: 90 percent / AlCl3; HCl / nitrobenzene / 10 h / 25 - 30 °C 3: 91 percent / acetone / 3 h 4: 95 percent / NaI; AlCl3 / acetonitrile / 3 h / 20 °C 5: 87 percent / dimethylformamide / 8 h / 15 °C View Scheme | |
Multi-step reaction with 8 steps 1: 82 percent / pyridine / 1 h / 20 °C 2: 84 percent / aluminum chloride / CH2Cl2 / 1 h / 15 - 20 °C 3: 70 percent aq. HClO4 / 1 h / 20 °C 4: H2O / 0.08 h / Heating 5: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr 6: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C 7: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C 8: 73 percent / CH2Cl2 / 1 h / 20 °C View Scheme |
2-chloro-5-methoxynitrobenzene
Iguratimod
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 84 percent / potassium tert-butoxide / dimethylformamide / 4 h / 110 °C 2: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C 3: 82 percent / pyridine / 1 h / 20 °C 4: 90 percent / AlCl3; HCl / nitrobenzene / 10 h / 25 - 30 °C 5: 91 percent / acetone / 3 h 6: 95 percent / NaI; AlCl3 / acetonitrile / 3 h / 20 °C 7: 87 percent / dimethylformamide / 8 h / 15 °C View Scheme | |
Multi-step reaction with 10 steps 1: 84 percent / potassium tert-butoxide / dimethylformamide / 4 h / 110 °C 2: 72 percent / 4N aq. HCl; Fe / ethanol / 0.33 h / 65 - 70 °C 3: 82 percent / pyridine / 1 h / 20 °C 4: 84 percent / aluminum chloride / CH2Cl2 / 1 h / 15 - 20 °C 5: 70 percent aq. HClO4 / 1 h / 20 °C 6: H2O / 0.08 h / Heating 7: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr 8: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C 9: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C 10: 73 percent / CH2Cl2 / 1 h / 20 °C View Scheme |
N-(5-methoxy-2-phenoxyphenyl)methanesulfonamide
Iguratimod
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 90 percent / AlCl3; HCl / nitrobenzene / 10 h / 25 - 30 °C 2: 91 percent / acetone / 3 h 3: 95 percent / NaI; AlCl3 / acetonitrile / 3 h / 20 °C 4: 87 percent / dimethylformamide / 8 h / 15 °C View Scheme | |
Multi-step reaction with 7 steps 1: 84 percent / aluminum chloride / CH2Cl2 / 1 h / 15 - 20 °C 2: 70 percent aq. HClO4 / 1 h / 20 °C 3: H2O / 0.08 h / Heating 4: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr 5: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C 6: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C 7: 73 percent / CH2Cl2 / 1 h / 20 °C View Scheme |
methyl 2-hydroxy-4-methylsulfonylamino-5-phenoxyphenyl ketone
Iguratimod
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 70 percent aq. HClO4 / 1 h / 20 °C 2: H2O / 0.08 h / Heating 3: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr 4: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C 5: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C 6: 73 percent / CH2Cl2 / 1 h / 20 °C View Scheme |
7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one
Iguratimod
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: H2 / 5 percent Pd/C / acetic acid / 1 h / 40 - 45 °C / 760 Torr 2: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C 3: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C 4: 73 percent / CH2Cl2 / 1 h / 20 °C View Scheme |
N-(4-oxo-6-phenoxy-2,3-dihydro-4H-7-chromenyl)methanesulfonamide
Iguratimod
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 97 percent / Br2 / CHCl3 / 0.5 h / 25 - 30 °C 2: 80 percent / NaN3; DMF / 1 h / 70 - 75 °C 3: 73 percent / CH2Cl2 / 1 h / 20 °C View Scheme |
Molecular Structure of Methanesulfonamide,N-[3-(formylamino)-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl]- (CAS NO.123663-49-0):
Molecular Formula: C17H14N2O6S
Molecular Weight: 374.3679
IUPAC Name: N-[7-(Methanesulfonamido)-4-oxo-6-phenoxychromen-3-yl]formamide
Synonyms of Methanesulfonamide,N-[3-(formylamino)-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl]- (CAS NO.123663-49-0): Iguratimod [INN] ; 3-Formylamino-7-methylsulfonylamino-6-phenoxy-4H-1-benzopyran-4-one ; Iguratimod ; N-(7-((Methylsulfonyl)amino)-4-oxo-6-phenoxy-4H-1-benzopyran-3-yl)formamide ; T 614 ; T-614 ; UNII-4IHY34Y2NV
CAS NO: 123663-49-0
Classification Code: API ; Pharmaceutical intermediate ; Pharmaceuticals
Index of Refraction: 1.673
Molar Refractivity: 92.3 cm3
Molar Volume: 246 cm3
Surface Tension: 72.3 dyne/cm
Density: 1.52 g/cm3
Flash Point: 304.9 °C
Enthalpy of Vaporization: 86.84 kJ/mol
Boiling Point: 580.6 °C at 760 mmHg
Vapour Pressure of Methanesulfonamide,N-[3-(formylamino)-4-oxo-6-phenoxy-4H-1-benzopyran-7-yl]- (CAS NO.123663-49-0): 1.8E-13 mmHg at 25°C