Potassium Chloride → 3-(5-Chloropyridin-2-yl)-5-(1-hydroxy-1-methylethyl)-N-{(1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethyl}benzamide

HRID 888410Notes

Reaction equation

HRID 888410 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:14]=[C:15]([C:17]([OH:20])([CH3:19])[CH3:18])[CH:16]=2)[C:11]([OH:13])=O)=[N:6][CH:7]=1.[Cl-].[K+].[O-:23][N+:24]1[C:29]([C:30]([F:33])([F:32])[F:31])=[CH:28][CH:27]=[C:26]([C@H:34]([NH2:36])[CH3:35])[CH:25]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(NC(C)C)(C)C>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:14]=[C:15]([C:17]([OH:20])([CH3:19])[CH3:18])[CH:16]=2)[C:11]([NH:36][C@@H:34]([C:26]2[CH:25]=[N+:24]([O-:23])[C:29]([C:30]([F:31])([F:32])[F:33])=[CH:28][CH:27]=2)[CH3:35])=[O:13])=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 4873Potassium ChlorideHCID 7912DiisopropylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59539683(1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethanamineHCID 68500303HCID 68500303, compound

Product 1

HCID 426030333-(5-Chloropyridin-2-yl)-5-(1-hydroxy-1-methylethyl)-N-{(1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethyl}benzamideYield 74.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(5-chloropyridin-2-yl)-5-(1-hydroxy-1-methylethyl)benzoic acid (20 mg, 0.07 mmol) in DMF (0.7 mL) were added the potassium chloride salt of (1R)-1-[1-oxido-6-(trifluoromethyl)pyridin-3-yl]ethanamine (33.6 mg, 0.09 mmol), HATU (0.05 M in DMA; 0.21 mL, 0.10 mmol) and diisopropylamine (60 μL, 0.34 mmol). The mixture was stirred at ambient temperature. After 30 min, the mixture was filtered and the filtrate was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (25 mg). FIRMS 480.1302 (M+1). 1H NMR (400 MHz, CDCl3): δ 8.58 (s, 1H); 8.36 (s, 1H); 8.20 (d, J=4.9 Hz, 2H); 8.04 (s, 1H); 7.78-7.61 (m, 3H); 7.42-7.30 (m, 2H); 5.33-5.23 (m, 1H); 1.69 (s, 6H), 1.63 (d, J=7.1 Hz, 3H).

Workup

  1. filtrationthe mixture was filtered
  2. customthe filtrate was purified by reverse phase chromatography (C-18, 95% water/acetonitrile→25% water/acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-882cd823761c4c21856bd522fad6c37d
Source dataset
uspto-grants-2012_08
Patent number
US08247401B2

Reaction notes

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