1-methyl-3-nitro-1H-pyrazole
A
1,1'-dimethyl-3-azoxypyrazole
B
methyl-1 amino-3 pyrazole
Conditions | Yield |
---|---|
With hydrazine hydrate; nickel In ethanol Heating; | A 54% B 7.1 g |
4-iodo-1-methyl-3-nitro-1H-pyrazole
methyl-1 amino-3 pyrazole
Conditions | Yield |
---|---|
With hydrogenchloride; tin(ll) chloride In water at 30℃; for 2h; Reduction; | 51% |
N-(1-methyl-3-pyrazolyl)-acetoacetamide
A
2,4-dimethyl-2H-pyrazolo<3,4-b>pyridin-6(7H)-one
B
methyl-1 amino-3 pyrazole
Conditions | Yield |
---|---|
With hydrogenchloride In ethanol for 3h; Heating; | A 21% B 15% |
1-methyl-3-nitro-1H-pyrazole
methyl-1 amino-3 pyrazole
Conditions | Yield |
---|---|
With hydrogenchloride; tin(ll) chloride Reduction; | |
With hydrogen In methanol for 3h; |
Conditions | Yield |
---|---|
With dmap; triethylamine In dichloromethane at 0 - 20℃; | 100% |
Conditions | Yield |
---|---|
In tetrahydrofuran at 20℃; for 2h; | 100% |
In tetrahydrofuran at 0 - 20℃; for 2h; | 100% |
Conditions | Yield |
---|---|
With pyridine In chloroform at 20℃; for 48h; chemoselective reaction; | 99% |
Conditions | Yield |
---|---|
With pyridine In chloroform at 20℃; for 48h; chemoselective reaction; | 99% |
Conditions | Yield |
---|---|
With copper(l) iodide; N-(2,6-dimethylphenyl)-6-hydroxypicolinamide; potassium carbonate In dimethyl sulfoxide at 110℃; | 99% |
2,5-hexanedione
methyl-1 amino-3 pyrazole
3-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazole
Conditions | Yield |
---|---|
toluene-4-sulfonic acid In toluene for 4h; Reflux; | 98% |
With acetic acid In toluene at 155℃; | 98.1% |
With toluene-4-sulfonic acid In benzene at 115℃; for 4h; | 94% |
methyl-1 amino-3 pyrazole
3-(2,5-dimethyl-1H-pyrrol-1-yl)-1-methyl-1H-pyrazole
Conditions | Yield |
---|---|
With acetic acid In toluene at 155℃; | 98.1% |
methyl-1 amino-3 pyrazole
Conditions | Yield |
---|---|
With copper(l) iodide; N-(2,6-dimethylphenyl)-6-hydroxypicolinamide; potassium carbonate In dimethyl sulfoxide at 110℃; | 98% |
6-bromo-2-methoxypyridine
methyl-1 amino-3 pyrazole
Conditions | Yield |
---|---|
With copper(l) iodide; N-(2,6-dimethylphenyl)-6-hydroxypicolinamide; potassium carbonate In dimethyl sulfoxide at 110℃; | 98% |
4-chloro-7-isothiocyanato-7-de(acetamide)colchicine
methyl-1 amino-3 pyrazole
4-chloro-N-[(1-methylpyrazole-3-yl)thiocarbamoyl]deacetyl colchicine
Conditions | Yield |
---|---|
In N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere; | 96% |
methyl-1 amino-3 pyrazole
Conditions | Yield |
---|---|
With hexafluorophosphoric acid; isopentyl nitrite In methanol at -20℃; for 1h; | 95% |
5-chloro-2-methylphenylisothiocyanate
methyl-1 amino-3 pyrazole
1-(5-chloro-2-methyl-phenyl)-3-(1-methyl-1H-pyrazol-3-yl)-thiourea
Conditions | Yield |
---|---|
95% |
(E)-(3-chloro-4-methanesulfonyl-phenyl)-isobutoxyimino-acetic acid
methyl-1 amino-3 pyrazole
(E)-2-(3-chloro-4-methanesulfonyl-phenyl)-2-isobutoxyimino-N-(1-methyl-1H-pyrazol-3-yl)-acetamide
Conditions | Yield |
---|---|
Stage #1: (E)-(3-chloro-4-methanesulfonyl-phenyl)-isobutoxyimino-acetic acid; methyl-1 amino-3 pyrazole With N-ethyl-N,N-diisopropylamine; HATU In dichloromethane at 0℃; for 2h; Stage #2: With sodium hydrogencarbonate In water | 95% |
2-chloro-5-fluoro-4-(3-nitrophenoxy)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine
methyl-1 amino-3 pyrazole
5-fluoro-N-(1-methyl-1H-pyrazol-3-yl)-4-(3-nitrophenoxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-2-amine
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 140℃; for 0.75h; Inert atmosphere; Microwave irradiation; | 95% |
methyl-1 amino-3 pyrazole
Conditions | Yield |
---|---|
In toluene for 1h; Reflux; | 94% |
methyl-1 amino-3 pyrazole
Conditions | Yield |
---|---|
With dihydrogen peroxide; iodine In ethanol; water at 15 - 35℃; for 6h; | 93.1% |
methyl-1 amino-3 pyrazole
5-methylpyrazolodithiazolium chloride
Conditions | Yield |
---|---|
With disulfur dichloride In acetic acid 1) 0 deg C to ambient temp. 2) up to 65 deg C, 3h 3) 65 deg C, 2h; | 93% |
2-(1-((tert-butoxycarbonyl)amino)cyclobutyl)-2-hydroxyacetic acid
methyl-1 amino-3 pyrazole
{1-[hydroxy-(1-methyl-1H-pyrazol-3-ylcarbamoyl)methyl]cyclobutyl}carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
Stage #1: 2-(1-((tert-butoxycarbonyl)amino)cyclobutyl)-2-hydroxyacetic acid; methyl-1 amino-3 pyrazole With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: With HATU In N,N-dimethyl-formamide at 20℃; for 2h; | 92% |
Stage #1: 2-(1-((tert-butoxycarbonyl)amino)cyclobutyl)-2-hydroxyacetic acid; methyl-1 amino-3 pyrazole With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.166667h; Stage #2: With HATU In N,N-dimethyl-formamide at 20℃; for 2h; | 92% |
2-(1-(tert-butoxycarbonylamino)-3,3-difluorocyclobutyl)-2-hydroxyacetic acid
methyl-1 amino-3 pyrazole
{3,3-difluoro-1-[hydroxy-(1-methyl-1H-pyrazol-3-ylcarbamoyl)methyl]cyclobutyl}carbamic acid tert-butyl ester
Conditions | Yield |
---|---|
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 2h; | 92% |
ethyl (2-chloroaceto)acetate
methyl-1 amino-3 pyrazole
5-Chloromethyl-1-methyl-1H-pyrazolo[1,5-a]pyrimidin-7-one
Conditions | Yield |
---|---|
With PPA at 100℃; | 91% |
3-[(1S)-2-tert-butoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzoic acid
methyl-1 amino-3 pyrazole
3-[(1S)-2-tert-butoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)-5-[4-(methylsulfonyl)phenoxy]benzamide
Conditions | Yield |
---|---|
Stage #1: 3-[(1S)-2-tert-butoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzoic acid With 1,1'-carbonyldiimidazole In acetonitrile at 25℃; for 2h; Stage #2: methyl-1 amino-3 pyrazole In acetonitrile at 60℃; for 18h; Product distribution / selectivity; | 91% |
Stage #1: 3-[(1S)-2-tert-butoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]benzoic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 1.08333h; Stage #2: methyl-1 amino-3 pyrazole In tetrahydrofuran; toluene at 60℃; for 18h; Product distribution / selectivity; |
3-[4-(azetidin-1-ylcarbonyl)phenoxy]-5-[(1S)-2-tert-butoxy-1-methylethoxy]benzoic acid
methyl-1 amino-3 pyrazole
3-[4-(Azetidin-1-ylcarbonyl)phenoxy]-5-[(1S)-2-tert-butoxy-1-methylethoxy]-N-(1-methyl-1H-pyrazol-3-yl)benzamide
Conditions | Yield |
---|---|
Stage #1: 3-[4-(azetidin-1-ylcarbonyl)phenoxy]-5-[(1S)-2-tert-butoxy-1-methylethoxy]benzoic acid With 4-methyl-morpholine; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine In acetonitrile at 0 - 20℃; for 1.3h; Stage #2: methyl-1 amino-3 pyrazole In acetonitrile at 20℃; for 0.333333h; Product distribution / selectivity; | 90% |
Stage #1: 3-[4-(azetidin-1-ylcarbonyl)phenoxy]-5-[(1S)-2-tert-butoxy-1-methylethoxy]benzoic acid With 1,1'-carbonyldiimidazole In acetonitrile at 25℃; for 1.08333h; Stage #2: methyl-1 amino-3 pyrazole In acetonitrile at 50℃; Product distribution / selectivity; | 89% |
methyl-1 amino-3 pyrazole
4-bromo-1-methyl-1H-pyrazol-3-ylamine
Conditions | Yield |
---|---|
With bromine In ethanol at 0 - 15℃; for 1h; | 89.4% |
With sodium hydroxide; bromine In dichloromethane; water |
Conditions | Yield |
---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 15℃; for 12h; | 89.2% |
ortho-bromophenylacetic acid
methyl-1 amino-3 pyrazole
2-(2-bromophenyl)-N-(1-methyl-1H-pyrazol-3-yl)acetamide
Conditions | Yield |
---|---|
Stage #1: ortho-bromophenylacetic acid With oxalyl dichloride In dichloromethane at 0 - 20℃; for 2h; Stage #2: methyl-1 amino-3 pyrazole In dichloromethane at 0 - 20℃; | 88% |
methyl-1 amino-3 pyrazole
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; sodium t-butanolate In toluene at 90℃; for 18h; Buchwald-Hartwig Coupling; Inert atmosphere; Sealed tube; | 88% |
Conditions | Yield |
---|---|
In acetic acid for 4h; Heating; | 87.4% |
di(tert-butyl)chlorophosphine
methyl-1 amino-3 pyrazole
P,P-di(tert-butyl)-N-(1-methyl-1H-pyrazol-3-yl)phosphinous amide
Conditions | Yield |
---|---|
With triethylamine at 125℃; for 72h; Inert atmosphere; | 87% |
methyl-1 amino-3 pyrazole
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In toluene at 85℃; for 2h; Buchwald-Hartwig Coupling; Inert atmosphere; | 87% |
tert-butyl {3-[(2-chloro-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidin-4-yl)oxy]phenyl}carbamate
methyl-1 amino-3 pyrazole
Conditions | Yield |
---|---|
With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene In 1,4-dioxane at 140℃; for 0.75h; Buchwald-Hartwig Coupling; Microwave irradiation; | 87% |
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