Sodium hydride → HCID 86762209, compound

HRID 467867Notes

Reaction equation

HRID 467867 reaction equation
CN1C(C)=[C:9]2[C:4]([N:5]([CH3:15])[C:6](=[O:14])[N:7]([CH3:13])[C:8]2=[O:12])=N1.Br[CH2:17][C:18]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26]2[CH:31]=[C:30]([F:32])[C:29]([O:33][CH2:34][C:35]([F:38])([F:37])[F:36])=[C:28]([F:39])[CH:27]=2)[N:25]=1)=[O:19].[H-].[Na+]>CN(C=O)C>[F:39][C:28]1[CH:27]=[C:26]([C:24]2[N:25]=[C:21]([NH:20][C:18](=[O:19])[CH2:17][N:25]3[C:9]4[C:8](=[O:12])[N:7]([CH3:13])[C:6](=[O:14])[N:5]([CH3:15])[C:4]=4[CH:23]=[C:24]3[CH3:26])[S:22][CH:23]=2)[CH:31]=[C:30]([F:32])[C:29]=1[O:33][CH2:34][C:35]([F:38])([F:37])[F:36]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 53675961HCID 53675961, compoundHCID 86662193HCID 86662193, compound

Product 1

HCID 86762209HCID 86762209, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the general procedure (Method A) by coupling Intermediate 2 (50 mg, 0.258 mmol) with 2-bromo-N-{4-(3,5-difluoro-4-(2,2,2-trifluoroethoxy)phenyl)-1,3-thiazol-2-yl}acetamide (133 mg, 0.308 mmol) in the presence of NaH (16 mg, 0.375 mmol) in dry DMF (5.0 mL) to give 60 mg of the product as a white solid; 1H NMR (δ ppm, 300 MHz, DMSO-d6) 2.26 (s, 3H), 3.16 (s, 3H), 3.34 (s, 3H), 4.80-4.90 (m, 2H), 5.33 (s, 2H), 6.07 (s, 1H), 7.71 (d, J=9.3 Hz, 2H), 7.83 (s, 1H), 12.75 (br s, 1H); ESI-MS (m/z) 544.55 (M+H)+.

Sources & evidence

ORD record
ord-95bd783d8d664e6e94fa9fcdece88827
Source dataset
uspto-grants-2014_01
Patent number
US08623880B2

Reaction notes

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