Diisopropylethylamine → 3-Fluoro-N-(1-{[4-iodo-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-4-pyridinecarboxamide

HRID 1946408Notes

Reaction equation

HRID 1946408 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([OH:10])=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:3]=[N:4][CH:5]=[CH:6][C:7]=1[C:8]([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:10]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 3453613-Fluoropyridine-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 595478541-{[4-Iodo-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-amine

Product 1

HCID 595480203-Fluoro-N-(1-{[4-iodo-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-yl)-4-pyridinecarboxamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent2×

Procedure

To 3-fluoro-4-pyridinecarboxylic acid (38 mg, 0.269 mmol, Aldrich) was added a solution of HATU (100 mg, 0.263 mmol, Advanced asymmetrics) in DMF (0.5 ml), DIPEA (0.11 ml, 0.630 mmol) and then a solution of 1-{[4-iodo-2-(trifluoromethyl)phenyl]methyl}-1H-pyrazol-3-amine (for a preparation see Intermediate 39)(75 mg, 0.204 mmol) in DMF (0.5 ml). The resulting orange 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 (86 mg); LCMS: (System 4) MH+=491, tRET=3.0 min.

Workup

  1. custompurified by MDAP on Sunfire C18 column (Method B)
  2. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-d6b05ec762a2465c86ce95eced65a7b2
Source dataset
uspto-grants-2013_03
Patent number
US08399436B2

Reaction notes

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