Sodium hydride → HCID 86762208, compound

HRID 467866Notes

Reaction equation

HRID 467866 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]([CH3:38])([CH3:37])[CH3:36])=[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]([CH3:38])([CH3:37])[CH3:36]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 53675961HCID 53675961, compoundHCID 86662190HCID 86662190, compound

Product 1

HCID 86762208HCID 86762208, 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-[4-(2,2-dimethylpropoxy)-3,5-difluorophenyl]-1,3-thiazol-2-yl}acetamide (130 mg, 0.310 mmol) in the presence of NaH (15 mg, 0.625 mmol) in dry DMF (5.0 mL) to give 55 mg of the product as a white solid; 1H NMR (δ ppm, 300 MHz, DMSO-d6) 1.01 (s, 9H), 2.26 (s, 3H), 3.17 (s, 3H), 3.34 (s, 3H), 3.80 (s, 2H), 5.33 (s, 2H), 6.07 (s, 1H), 7.63 (s, 1H), 7.66 (s, 1H), 7.77 (s, 1H), 12.74 (br s, 1H); ESI-MS (m/z) 532.24 (M+H)+.

Sources & evidence

ORD record
ord-6b7f69d9307640579472b5ca0d84782d
Source dataset
uspto-grants-2014_01
Patent number
US08623880B2

Reaction notes

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