7-Trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid → HCID 16068664, compound

HRID 1784570Notes

Reaction equation

HRID 1784570 reaction equation
[F:1][C:2]([F:26])([F:25])[C:3]1[N:8]2[N:9]=[CH:10][C:11]([C:12](O)=O)=[C:7]2[N:6]=[C:5]([C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[CH:4]=1.[OH:27][NH:28][C:29](=[NH:36])[C:30]1[CH:35]=[CH:34][CH:33]=[N:32][CH:31]=1>>[N:32]1[CH:33]=[CH:34][CH:35]=[C:30]([C:29]2[N:36]=[C:12]([C:11]3[CH:10]=[N:9][N:8]4[C:3]([C:2]([F:26])([F:25])[F:1])=[CH:4][C:5]([C:15]5[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][CH:16]=5)=[N:6][C:7]=34)[O:27][N:28]=2)[CH:31]=1

Participants

3

Reactant 2

HCID 866071127-Trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acidHCID 178513339HCID 178513339, compound

Product 1

HCID 16068664HCID 16068664, compound

Procedure

The title compound was prepared from 7-trifluoromethyl-5-(4-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid (example C.2) (188 mg, 0.5 mmol) and commercially available N-hydroxy-nicotinamidine [CAS-No. 1594-58-7] (103 mg, 0.75 mmol) according to general procedure II. Obtained after purification by column chromatography (dichloromethane/MeOH/NH4OH) and crystallization (dichloromethane/MeOH/hexane) as a yellow solid (126 mg, 53%). MS (EI) 476.1 [(M+H)+]; mp 199° C.

Workup

  1. customObtained
  2. customafter purification
  3. customby column chromatography (dichloromethane/MeOH/NH4OH) and crystallization (dichloromethane/MeOH/hexane) as a yellow solid (126 mg, 53%)

Sources & evidence

ORD record
ord-ba218c3467ee4366a1ad32eea9619761
Source dataset
uspto-grants-2009_03
Patent number
US07504404B2

Reaction notes

Loading…