2-Amino-4-chlorophenol → HCID 19414466, compound
Reaction equation
N1N2C=CC=NC2=C(C(O)=O)C=1.NC1C=C(Cl)C=CC=1O.[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([O:29]C(C2C=NN3C=CC=NC=23)=O)=[C:25]([NH:41][C:42]([C:44]2[CH:45]=[N:46][N:47]3[CH:52]=[CH:51][CH:50]=[N:49][C:48]=23)=[O:43])[CH:24]=1>S(Cl)(Cl)=O>[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([NH:41][C:42]([C:44]2[CH:45]=[N:46][N:47]3[CH:52]=[CH:51][CH:50]=[N:49][C:48]=23)=[O:43])[CH:24]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 85 °C
Procedure
Pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (0.5 g, 3.06 mmol) was suspended in thionyl chloride (25 mL) and the resulting mixture was heated at 85° C. for 1.5 hours. The volatiles were then evaporated under high vacuum and the residue was suspended in pyridine (25 mL). 2-Amino-4-chlorophenol (0.46 g, 3.2 mmol) was added and the resulting mixture was heated at reflux overnight. The volatiles were then evaporated under high vacuum, water and dichloromethane were added to the residue and the mixture was evaporated under reduced pressure. The solid residue was washed with a mixture of dichloromethane and methanol (96/4) to give 0.588 g (67% yield) of pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (5-chloro-2-hydroxy-phenyl)-amide in mixture with pyrazolo[1,5-a]pyrimidine-3-carboxylic acid 4-chloro-2-[(pyrazolo[1,5-a]pyrimidine-3-carbonyl)-amino]-phenyl ester.
Workup
- customThe volatiles were then evaporated under high vacuum
- temperaturethe resulting mixture was heated
- temperatureat reflux overnight
- customThe volatiles were then evaporated under high vacuum, water and dichloromethane
- additionwere added to the residue
- customthe mixture was evaporated under reduced pressure
- washThe solid residue was washed with a mixture of dichloromethane and methanol (96/4)
Sources & evidence
- ORD record
- ord-88c25407f6d34ad39b21663a1a3a1d64
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09255110B2
Reaction notes
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