Sodium hydride → HCID 46947049, compound

HRID 1467835Notes

Reaction equation

HRID 1467835 reaction equation
[CH3:1][N:2]1[C:7]2[C:8](C)=[CH:9][NH:10][C:6]=2[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14].Br[CH2:16][C:17]([NH:19][C:20]1[S:21][CH:22]=[C:23]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][C:26]=2[F:32])[N:24]=1)=[O:18].[H-].[Na+]>CN(C=O)C>[F:32][C:26]1[CH:27]=[C:28]([F:31])[CH:29]=[CH:30][C:25]=1[C:23]1[N:24]=[C:20]([NH:19][C:17](=[O:18])[CH2:16][N:10]2[C:6]3[C:5](=[O:12])[N:4]([CH3:13])[C:3](=[O:14])[N:2]([CH3:1])[C:7]=3[CH:8]=[CH:9]2)[S:21][CH:22]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66742610HCID 66742610, compoundHCID 86662181HCID 86662181, compound

Product 1

HCID 46947049HCID 46947049, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the general procedure (Method A) by coupling Intermediate 1 (50 mg, 0.279 mmol) with 2-bromo-N-[4-(2,4-difluorophenyl)-1,3-thiazol-2-yl]acetamide (111 mg, 0.330 mmol) in the presence of NaH (16 mg, 0.666 mmol) in dry DMF (5.0 mL) to give 60 mg of the product as a white solid; 1H NMR (δ ppm, DMSO-d6, 300 MHz) 3.17 (s, 3H), 3.40 (s, 3H), 5.32 (s, 2H), 6.23 (s, 1H), 7.21-7.27 (m, 1H), 7.36-7.42 (m, 2H), 7.52 (s, 1H), 8.03-8.10 (m, 1H), 12.70 (br s, 1H); APCI-MS (m/z) 432.20 (M+H)+.

Sources & evidence

ORD record
ord-a2848ba1c8f74486834e98a71458c4de
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

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