6646-51-1

Basic information

• Product Name: 1-methyl-1H-imidazol-2-amine
• Synonyms: 1-methyl-1H-imidazol-2-amine;1-Methyl-1H-imidazol-2-ylamine;1-Methyl-2-aminoimidazole;2-Amino-1-methylimidazole;1-methyl-1H-imidazol-2-amine(SALTDATA: HCl);2-AMino-1-Methyl-1H-iMidazole, 97%;1H-IMidazol-2-aMine,1-Methyl-;CAS:6646-51-1
• CAS NO: 6646-51-1
• Molecular Formula: C₄H₇N₃
• Molecular Weight: 97.1203
• Mol File: 6646-51-1.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 255℃
• Flash Point: 108℃
• Appearance: /
• Density: 1.22
• Vapor Pressure: 0.017mmHg at 25°C
• Refractive Index: 1.601
• Storage Temp.: Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
• PKA: 8.53±0.25(Predicted)
• CAS DataBase Reference: 1-methyl-1H-imidazol-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-1H-imidazol-2-amine(6646-51-1)
• EPA Substance Registry System: 1-methyl-1H-imidazol-2-amine(6646-51-1)

Safety Data

• Hazardous Substances Data: 6646-51-1(Hazardous Substances Data)

Usage

Uses

1-Methyl-1H-imidazol-2-amine, is an intermediate in the synthesis of variety of antibacterial and antitumor agents.

InChI:InChI=1/C4H7N3/c1-7-3-2-6-4(7)5/h2-3H,1H3,(H2,5,6)

Synthetic route

1H-imidazol-2-amine (7720-39-0) + methyl iodide (74-88-4) → 1-methyl-2-aminoimidazole (6646-51-1)

Conditions	Yield
With copper(l) iodide; 8-quinolinol; sodium t-butanolate In methanol at 50℃; for 36h; Solvent;	72%
Stage #1: 1H-imidazol-2-amine With tert-butyldimethylsilyl chloride Stage #2: methyl iodide With n-butyllithium

2-lithium-N-methylimidazole (51081-36-8) → 1-methyl-2-aminoimidazole (6646-51-1)

Conditions	Yield
With 1-azidostyrene In tetrahydrofuran for 2h; from -78 deg.C to room temp.;	45%

1-methyl-2-nitroimidazole (1671-82-5) → 1-methyl-2-aminoimidazole (6646-51-1)

Conditions	Yield
With iron; acetic acid at 80℃;	17%
With palladium 10% on activated carbon; hydrogen In 1,4-dioxane at 20℃; for 16h;	70 mg

bromocyane (506-68-3) + N-(methyl)aminoacetaldehyde dimethyl acetal (122-07-6) → 1-methyl-2-aminoimidazole (6646-51-1)

Conditions	Yield
Stage #1: bromocyane; N-(methyl)aminoacetaldehyde dimethyl acetal With acetic acid In water at 100℃; for 1h; Stage #2: With hydrogenchloride In water at 100℃; for 0.25h;

ethyl 2-imino-3-methyl-2,3-dihydro-1H-imidazole-1-carboxylate → 1-methyl-2-aminoimidazole (6646-51-1)

Conditions	Yield
With hydrogenchloride In methanol; water at 22℃; for 8h;

3-Bromopyridine (626-55-1) + 1-methyl-2-aminoimidazole (6646-51-1) → C9H10N4 (1369433-28-2)

Conditions	Yield
With [2-(di-tert-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl][2-((2-aminoethyl)phenyl)]palladium(II) chloride; sodium t-butanolate; tert-butyl XPhos In tert-butyl alcohol at 20℃; for 16h; Inert atmosphere;	97%

1-methyl-2-aminoimidazole (6646-51-1) + methyl iodide (74-88-4) → 2-amino-1,3-dimethylimidazolium iodide

Conditions	Yield
for 1h; 0 deg C to r.t.;	92%

1-methyl-2-aminoimidazole (6646-51-1) + (S)-3-(bromomethyl)-N-(cyclopropyl(4-fluoro-3-methylphenyl)methyl)-5-(2-(trifluoromethyl)pyridin-3-yl)benzamide → (S)-N-(cyclopropyl(4-fluoro-3-methylphenyl)methyl)-3-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)-5-(2-(trifluoromethyl)pyridin-3-yl)benzamide

Conditions	Yield
In acetonitrile at 23 - 50℃; for 12h;	84%

1-methyl-2-aminoimidazole (6646-51-1) + bromobenzene (108-86-1) → C10H11N3 (1369433-26-0)

Conditions	Yield
With [2-(di-tert-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl][2-((2-aminoethyl)phenyl)]palladium(II) chloride; sodium t-butanolate; tert-butyl XPhos In tert-butyl alcohol at 20℃; for 4h; Inert atmosphere;	83%

1-methyl-2-aminoimidazole (6646-51-1) + bis(2,4,6-trichlorophenyl) ethylmalonate (15781-72-3) → 1-methyl-6-ethyl-7-hydroxy-4,5-dihydroimidazo<1,2-a>pyrimidin-5-one

Conditions	Yield
at 160℃; for 0.05h;	81%

2-bromo-pyridine (109-04-6) + 1-methyl-2-aminoimidazole (6646-51-1) → C9H10N4 (1369433-27-1)

Conditions	Yield
With [2-(di-tert-butylphosphino)-2′,4′,6′-triisopropyl-1,1′-biphenyl][2-((2-aminoethyl)phenyl)]palladium(II) chloride; sodium t-butanolate; tert-butyl XPhos In tert-butyl alcohol at 20℃; for 16h; Inert atmosphere;	80%

1-methyl-2-aminoimidazole (6646-51-1) + 4-chlorobenzoyl chloride (586-75-4) → 4-bromo-N-(1-methyl-1H-imidazol-2-yl)benzamide

Conditions	Yield
With potassium hydrogencarbonate In ethanol at 50℃; for 12h;	77%

1-methyl-2-aminoimidazole (6646-51-1) + 4-hydroxy-8-trifluoromethyl-3-quinoline-carboxylic acid chloride (59197-85-2) → 4-Hydroxy-8-trifluoromethyl-quinoline-3-carboxylic acid (1-methyl-1H-imidazol-2-yl)-amide (114350-72-0)

Conditions	Yield
With pyridine Ambient temperature;	72%

1-methyl-2-aminoimidazole (6646-51-1) + 3-(bromomethyl)-N-(3,4-dichlorobenzyl)-5-(6-fluoro-2-methylpyridin-3-yl)benzamide → N-(3,4-dichlorobenzyl)-3-(6-fluoro-2-methylpyridin-3-yl)-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)benzamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 80℃; for 18h;	62%

1-methyl-2-aminoimidazole (6646-51-1) + 7-(bromomethyl)-2-(4-chloro-3-methylbenzyl)-5-(2-methylpyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one + trifluoroacetic acid (76-05-1) → (x)C2HF3O2*C28H28ClN5O

Conditions	Yield
Stage #1: 1-methyl-2-aminoimidazole; 7-(bromomethyl)-2-(4-chloro-3-methylbenzyl)-5-(2-methylpyridin-3-yl)-3,4-dihydroisoquinolin-1(2H)-one at 80℃; for 0.5h; Stage #2: trifluoroacetic acid With Phenomenex Gemini Cl 8 In water; acetonitrile	56%

1-methyl-2-aminoimidazole (6646-51-1) + di-tert-butyl dicarbonate (24424-99-5) + 3-bromo-5-(bromomethyl)-N-(3,4-dichlorobenzyl)benzamide → tert-butyl (E)-(1-(3-bromo-5-((3,4-dichlorobenzyl)carbamoyl)benzyl)-3-methyl-1,3-dihydro-2H-imidazol-2-ylidene)carbamate

Conditions	Yield
Stage #1: 1-methyl-2-aminoimidazole; 3-bromo-5-(bromomethyl)-N-(3,4-dichlorobenzyl)benzamide With N-ethyl-N,N-diisopropylamine In acetonitrile for 18h; Reflux; Stage #2: di-tert-butyl dicarbonate With dmap In tetrahydrofuran at 20℃; for 18h;	53%

1-methyl-2-aminoimidazole (6646-51-1) + C17H12F2N4O2 → C21H17F2N7O

Conditions	Yield
With 2-(1H-9-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 24h;	48%

1-methyl-2-aminoimidazole (6646-51-1) + 2-(Dichloromethyl)-4-hydroxy-8-(trifluoromethyl)-3-quinolinecarboxylic acid ethyl ester (80777-17-9) → 685B (80777-33-9)

Conditions	Yield
	42%

1-methyl-2-aminoimidazole (6646-51-1) + 5-(bromomethyl)-N-(3,4-dichlorobenzyl)-2',4'-difluoro-6'-methyl-[1,1'-biphenyl]-3-carboxamide → N-(3,4-dichlorobenzyl)-2′,4′-difluoro-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazo-1-yl)methyl)-6′-methyl-[1,1′-biphenyl]-3-carboxamide

Conditions	Yield
In acetonitrile at 80℃; for 0.5h; Microwave irradiation;	40%

1-methyl-2-aminoimidazole (6646-51-1) + 2,8-bis-(trifluoromethyl)-4-hydroxy-3-quinoline-carboxylic acid chloride (75999-37-0) → 2,8-bis-(trifluoromethyl)-4-hydroxy-N-(1-methyl-1H-imidazol-2-yl)-3-quinolinecarboxamide (75999-41-6)

Conditions	Yield
With pyridine Ambient temperature;	34%

1-methyl-2-aminoimidazole (6646-51-1) + 3-(bromomethyl)-N-(3,5-dimethoxybenzyl)-5-(6-fluoro-4-methylpyridin-3-yl)benzamide → N-(3,5-dimethoxybenzyl)-3-(6-fluoro-4-methylpyridin-3-yl)-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)benzamide

Conditions	Yield
In acetonitrile at 80℃; for 16h;	20%

1-methyl-2-aminoimidazole (6646-51-1) + 7-methoxyquinoline-3-carboxylic acid (474659-26-2) → 7-methoxy-N-(1-methyl-1H-imidazol-2-yl)quinoline-3-carboxamide

Conditions	Yield
Stage #1: 7-methoxyquinoline-3-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 20℃; for 0.0833333h; Stage #2: 1-methyl-2-aminoimidazole In N,N-dimethyl-formamide	12%

1-methyl-2-aminoimidazole (6646-51-1) + ethyl 4-hydroxy-2-ethyl-8-trifluoromethyl-quinoline-3-carboxylate (64321-74-0) → 2-Ethyl-4-hydroxy-8-trifluoromethyl-quinoline-3-carboxylic acid (1-methyl-1H-imidazol-2-yl)-amide (114350-79-7)

Conditions	Yield
	10%

1-methyl-2-aminoimidazole (6646-51-1) + (S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid (26250-84-0) → tert-butyl (2S)-2-[(1-methylimidazol-2-yl)carbamoyl]piperidine-1-carboxylate

Conditions	Yield
Stage #1: (S)-(-)-1-(tert-butoxycarbonyl)-2-piperidinecarboxylic acid With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 0.0833333h; Stage #2: 1-methyl-2-aminoimidazole In dichloromethane at 20℃; for 5h;	10%

1-methyl-2-aminoimidazole (6646-51-1) + (S)-(5-((cyclopropyl(4-methylpyridin-2-yl)methyl)carbamoyl)-4'-fluoro-2'-methyl-[1,1'-biphenyl]-3-yl)methyl methanesulfonate → (S)-N-(cyclopropyl(4-methylpyridin-2-yl)methyl)-4'-fluoro-5-((2-imino-3-methyl-2,3-dihydro-1H-imidazol-1-yl)methyl)-2'-methyl-[1,1'-biphenyl]-3-carboxamide

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In acetonitrile at 55℃; for 16h;	9%

1-methyl-2-aminoimidazole (6646-51-1) + (R)-(-)-3-[3-fluoro-4-(3,6-dihydro-2H-pyran-4-yl)phenyl]-5-[[(methylsulfonyl)oxy]methyl]-2-oxazolidinone (188975-34-0) → 5(S)-(N-methylimidazol-2-ylaminomethyl)-3-(3-fluoro-4-(3,6-dihydro-(2H)-pyran-4-yl)phenyl)oxazolidin-2-one

Conditions	Yield
Stage #1: 1-methyl-2-aminoimidazole With n-butyllithium In tetrahydrofuran; water at -78℃; for 1h; Stage #2: (R)-(-)-3-[3-fluoro-4-(3,6-dihydro-2H-pyran-4-yl)phenyl]-5-[[(methylsulfonyl)oxy]methyl]-2-oxazolidinone In tetrahydrofuran; water at 20℃; for 18h; Heating / reflux; Stage #3: With ammonium chloride In tetrahydrofuran; water	4.6%

1-methyl-2-aminoimidazole (6646-51-1) + C22H17Cl4N3O4 → (1‘R,2’S,7a’R)-5,7-dichloro-N1‘-(3,5-dichlorophenyl)-N2’-(1- methyl-1H-imidazol-2-yl)-2-oxo-1‘,2’,5’,6’,7’,7a’-hexahydrospiro[indoline-3,3’-pyrrolizine]-1‘,2’-dicarboxamide

Conditions	Yield
Stage #1: C22H17Cl4N3O4 With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0℃; for 0.5h; Stage #2: 1-methyl-2-aminoimidazole In tetrahydrofuran at 60℃; for 24h;	4%

1-methyl-2-aminoimidazole (6646-51-1) + orthoformic acid triethyl ester (122-51-0) + phosphonic acid diethyl ester (762-04-9) → [(diethoxy-phosphoryl)-(1-methyl-1H-imidazol-2-ylamino)-methyl]-phosphonic acid diethyl ester

Conditions	Yield
With phosphonic acid diethyl ester at 120 - 125℃; for 3h;

1-methyl-2-aminoimidazole (6646-51-1) + 5-chloro-6-(chloromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione (73742-45-7) → 5-chloro-6-{[2-imino-3-methyl(4-imidazolin-1-yl)]methyl}uracil hydrochloride

Conditions	Yield
In water at 100℃; for 1h;	80 mg

Upstream product

• 1671-82-5 1-methyl-2-nitroimidazole 
• 7720-39-0 1H-imidazol-2-amine 
• 74-88-4 methyl iodide 
• 51081-36-8 2-lithium-N-methylimidazole 
• 506-68-3 bromocyane 
• 122-07-6 N-(methyl)aminoacetaldehyde dimethyl acetal 

Downstream Products

• 1369433-26-0 C₁₀H₁₁N₃ 

Relevant articles and documents

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