2-Fluorobenzoic acid → 2-Fluoro-N-(1-{[4-iodo-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)benzamide
Reaction equation
[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[I:44][C:45]1[CH:50]=[CH:49][C:48]([CH2:51][N:52]2[CH:56]=[CH:55][C:54]([NH2:57])=[N:53]2)=[C:47]([C:58]([F:61])([F:60])[F:59])[CH:46]=1>CN(C=O)C.CO>[F:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:57][C:54]1[CH:55]=[CH:56][N:52]([CH2:51][C:48]2[CH:49]=[CH:50][C:45]([I:44])=[CH:46][C:47]=2[C:58]([F:61])([F:59])[F:60])[N:53]=1)=[O:6]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To 2-fluorobenzoic acid (22 mg, 0.157 mmol, Aldrich) was added a solution of HATU (58 mg, 0.153 mmol, Advanced asymmetrics) in DMF (0.5 ml), DIPEA (0.062 ml, 0.355 mmol) and then a solution of 1-{[4-iodo-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-amine (for a preparation see Intermediate 39)(43 mg, 0.117 mmol) in DMF (0.5 ml). The resulting yellow solution was stirred at ambient temperature overnight. The reaction mixture was diluted with methanol (1 ml) and purified by MDAP on Sunfire C18 column (Method B) using Acetonitrile-Water with a Formic acid modifier. The solvent was evaporated in vacuo to give the title compound as a white solid (40 mg); LCMS: (System 4) MH+=490, tRET=3.38 min.
Workup
- custompurified by MDAP on Sunfire C18 column (Method B)
- customThe solvent was evaporated in vacuo
Sources & evidence
- ORD record
- ord-6f147431838748278e1554e648f55ebc
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08399436B2
Reaction notes
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