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Cas:146362-70-1
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tert-butyl 2-(1-(7-chloroquinolin-4-yl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxamido)adamantane-2-carboxylate
merclinertant
Conditions | Yield |
---|---|
With QP-SA In dichloromethane at 18℃; for 20h; | 86% |
With trifluoroacetic acid In dichloromethane at 35℃; for 3.5h; |
merclinertant
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 3 h / 140 °C / Microwave irradiation 2: potassium hydroxide / water; tetrahydrofuran / 2 h / 120 °C / Microwave irradiation 3: N-ethyl-N,N-diisopropylamine; 2,6-dimethylpyridine; bis(trichloromethyl) carbonate / dichloromethane / 18 h / 20 °C 4: QP-SA / dichloromethane / 20 h / 18 °C View Scheme |
ethyl 1-(7-chloroquinolin-4-yl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxylate
merclinertant
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: potassium hydroxide / water; tetrahydrofuran / 2 h / 120 °C / Microwave irradiation 2: N-ethyl-N,N-diisopropylamine; 2,6-dimethylpyridine; bis(trichloromethyl) carbonate / dichloromethane / 18 h / 20 °C 3: QP-SA / dichloromethane / 20 h / 18 °C View Scheme | |
Multi-step reaction with 4 steps 1: sodium hydroxide; water / tetrahydrofuran 2: thionyl chloride / 3 h / 20 °C 3: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane; N,N-dimethyl-formamide / 20 °C 4: trifluoroacetic acid / dichloromethane / 3.5 h / 35 °C View Scheme |
2-amino-2-adamantanecarboxylic acid
merclinertant
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: perchloric acid / water / 6 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; 2,6-dimethylpyridine; bis(trichloromethyl) carbonate / dichloromethane / 18 h / 20 °C 3: QP-SA / dichloromethane / 20 h / 18 °C View Scheme |
2'-hydroxy-6'-methoxyacetophenone
merclinertant
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: methanol / 1 h / 160 °C 2: sodium ethanolate / ethanol / 0.42 h / 80 °C / Microwave irradiation 3: N,N-dimethyl-formamide / 3 h / 140 °C / Microwave irradiation 4: potassium hydroxide / water; tetrahydrofuran / 2 h / 120 °C / Microwave irradiation 5: N-ethyl-N,N-diisopropylamine; 2,6-dimethylpyridine; bis(trichloromethyl) carbonate / dichloromethane / 18 h / 20 °C 6: QP-SA / dichloromethane / 20 h / 18 °C View Scheme |
2,6-dimethoxyacetophenone
merclinertant
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: sodium ethanolate / ethanol / 0.42 h / 80 °C / Microwave irradiation 2: N,N-dimethyl-formamide / 3 h / 140 °C / Microwave irradiation 3: potassium hydroxide / water; tetrahydrofuran / 2 h / 120 °C / Microwave irradiation 4: N-ethyl-N,N-diisopropylamine; 2,6-dimethylpyridine; bis(trichloromethyl) carbonate / dichloromethane / 18 h / 20 °C 5: QP-SA / dichloromethane / 20 h / 18 °C View Scheme | |
Multi-step reaction with 6 steps 1: sodium / ethanol / 6 h / 20 °C 2: sulfuric acid / ethanol / 3 h / 20 - 100 °C / Microwave irradiation 3: sodium hydroxide; water / tetrahydrofuran 4: thionyl chloride / 3 h / 20 °C 5: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane; N,N-dimethyl-formamide / 20 °C 6: trifluoroacetic acid / dichloromethane / 3.5 h / 35 °C View Scheme |
1-(7-chloroquinolin-4-yl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carbonyl chloride
2-amino-adamantane-2-carboxylic acid tert-butyl ester
merclinertant
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane; N,N-dimethyl-formamide / 20 °C 2: trifluoroacetic acid / dichloromethane / 3.5 h / 35 °C View Scheme |
2-Adamantanone
merclinertant
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: ammonia; ammonium chloride / ethanol; water / 8 h / 55 °C / pH > 10 2: potassium carbonate / tetrahydrofuran; water / 1.5 h / 20 °C 3: hydrogenchloride; water / tetrahydrofuran / 18 h / 20 °C 4: hydrogenchloride / water; acetic acid / 72 h / Reflux 5: tetrafluoroboric acid / water / 48 h / 60 °C / Sealed tube 6: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane; N,N-dimethyl-formamide / 20 °C 7: trifluoroacetic acid / dichloromethane / 3.5 h / 35 °C View Scheme |
2-aminoadamantane-2-carbonitrile
merclinertant
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: potassium carbonate / tetrahydrofuran; water / 1.5 h / 20 °C 2: hydrogenchloride; water / tetrahydrofuran / 18 h / 20 °C 3: hydrogenchloride / water; acetic acid / 72 h / Reflux 4: tetrafluoroboric acid / water / 48 h / 60 °C / Sealed tube 5: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane; N,N-dimethyl-formamide / 20 °C 6: trifluoroacetic acid / dichloromethane / 3.5 h / 35 °C View Scheme |
2-benzamidoadamantane-2-carbonitrile
merclinertant
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: hydrogenchloride; water / tetrahydrofuran / 18 h / 20 °C 2: hydrogenchloride / water; acetic acid / 72 h / Reflux 3: tetrafluoroboric acid / water / 48 h / 60 °C / Sealed tube 4: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane; N,N-dimethyl-formamide / 20 °C 5: trifluoroacetic acid / dichloromethane / 3.5 h / 35 °C View Scheme |
2-benzamidoadamantane-2-carboxylic acid
merclinertant
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: hydrogenchloride / water; acetic acid / 72 h / Reflux 2: tetrafluoroboric acid / water / 48 h / 60 °C / Sealed tube 3: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane; N,N-dimethyl-formamide / 20 °C 4: trifluoroacetic acid / dichloromethane / 3.5 h / 35 °C View Scheme |
2-(amino)tricyclo[3.3.1.13,7]decane-2-carboxylic acid hydrochloride
merclinertant
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: tetrafluoroboric acid / water / 48 h / 60 °C / Sealed tube 2: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane; N,N-dimethyl-formamide / 20 °C 3: trifluoroacetic acid / dichloromethane / 3.5 h / 35 °C View Scheme |
ethyl 4-(2,6-dimethoxyphenyl)-4-hydroxy-2-oxobut-3-enoate
merclinertant
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: sulfuric acid / ethanol / 3 h / 20 - 100 °C / Microwave irradiation 2: sodium hydroxide; water / tetrahydrofuran 3: thionyl chloride / 3 h / 20 °C 4: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane; N,N-dimethyl-formamide / 20 °C 5: trifluoroacetic acid / dichloromethane / 3.5 h / 35 °C View Scheme |
1-(7-chloroquinolin-4-yl)-5-(2,6-dimethoxyphenyl)-1H-pyrazole-3-carboxylic acid
merclinertant
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: thionyl chloride / 3 h / 20 °C 2: N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate / dichloromethane; N,N-dimethyl-formamide / 20 °C 3: trifluoroacetic acid / dichloromethane / 3.5 h / 35 °C View Scheme |
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