1-[(5-Bromo-2-thienyl)sulfonyl]-4-methylpiperazine → 7-Difluoromethyl-3-[5-(4-methyl-piperazine-1-sulfonyl)-thiophen-2-ylethynyl]-5-(3-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine

HRID 269305Notes

Reaction equation

HRID 269305 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][N:6]2[C:11]([CH:12]([F:14])[F:13])=[CH:10][C:9]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)=[N:8][C:7]=12)#[CH:2].Br[C:26]1[S:30][C:29]([S:31]([N:34]2[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]2)(=[O:33])=[O:32])=[CH:28][CH:27]=1>>[F:13][CH:12]([F:14])[C:11]1[N:6]2[N:5]=[CH:4][C:3]([C:1]#[C:2][C:26]3[S:30][C:29]([S:31]([N:34]4[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]4)(=[O:32])=[O:33])=[CH:28][CH:27]=3)=[C:7]2[N:8]=[C:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:23])([F:24])[F:22])[CH:16]=2)[CH:10]=1

Participants

3

Reactant 2

HCID 6621571-[(5-Bromo-2-thienyl)sulfonyl]-4-methylpiperazineHCID 866080813-Ethynyl-7-difluoromethyl-5-(3-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine

Product 1

HCID 670007977-Difluoromethyl-3-[5-(4-methyl-piperazine-1-sulfonyl)-thiophen-2-ylethynyl]-5-(3-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine

Procedure

The title compound was prepared from 3-ethynyl-7-difluoromethyl-5-(3-trifluoromethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (example C.15) (169 mg, 0.5 mmol) and 1-(5-bromo-thiophene-2-sulfonyl)-4-methyl-piperazine (example B.50) (163 mg, 0.5 mmol) according to general procedure II. Obtained as a yellow solid (220 mg, 76%). MS (EI) 581.1 [(M)+]; mp 214° C.

Sources & evidence

ORD record
ord-5aaf388c589944f9ab3894c620727e8b
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

Loading…