Dimethyl Sulfoxide → HCID 118093088, compound

HRID 2207406Notes

Reaction equation

HRID 2207406 reaction equation
[OH-:1].[Na+].[F:3][C:4]([F:36])([F:35])[CH2:5][C:6]([CH3:34])([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[C:20]([NH:22][C:23]3[N:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][N:24]=3)[CH:19]=[C:18]([CH3:33])[CH:17]=2)=[CH:12][N:11]=1)[C:7]#N.CS(C)=[O:39]>CN(C=O)C>[F:3][C:4]([F:36])([F:35])[CH2:5][C@@:6]([C:7]([OH:39])=[O:1])([CH3:34])[NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[C:20]([NH:22][C:23]3[N:28]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:26]=[CH:25][N:24]=3)[CH:19]=[C:18]([CH3:33])[CH:17]=2)=[CH:12][N:11]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 14798Sodium HydroxideHCID 131735910HCID 131735910, compound

Product 1

HCID 118093088HCID 118093088, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydroxide (5 M, 33.3 μL, 0.167 mmol) was added to a mixture of 4,4,4-trifluoro-2-methyl-2-{[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]amino}butanenitrile (40.0 mg, 0.083 mmol) in DMSO (167 μL) and the reaction mixture was stirred at room temperature. Upon the reaction completion (monitored by LCMS) was diluted with DMF and filtered. The residue was directly purified by reverse phase chromatography and then by silica gel chromatography (0-100% ethyl acetate in hexanes) to yield 4,4,4-trifluoro-N-[5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridin-2-yl]isovaline. MS APCI calc'd for C22H20F6N5O2 [M+H]+ 500. found 500. 1H NMR (500 MHz, CDCl3) δ 8.60 (d, J=5.7 Hz, 1H), 8.07 (s, 1H), 7.95 (d, J=11.2 Hz, 1H), 7.54 (s, 1H), 7.43 (s, 1H), 7.10 (d, J=5.4 Hz, 1H), 6.90 (s, 1H), 6.72 (d, J=9.8 Hz, 1H), 3.04 (s, 1H), 2.59-2.24 (m, 4H), 1.98-1.81 (m, 3H).

Workup

  1. filtrationfiltered
  2. customThe residue was directly purified by reverse phase chromatography

Sources & evidence

ORD record
ord-2ff66e540588469a92eb626cc1219867
Source dataset
uspto-grants-2016_06
Patent number
US09376418B2

Reaction notes

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