Sodium hydride → HCID 46947247, compound

HRID 1467836Notes

Reaction equation

HRID 1467836 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])=[C:27]([C:32]([F:35])([F:34])[F:33])[CH:26]=2)[N:24]=1)=[O:18].[H-].[Na+]>CN(C=O)C>[CH3:1][N:2]1[C:7]2[CH:8]=[CH:9][N:10]([CH2:16][C:17]([NH:19][C:20]3[S:21][CH:22]=[C:23]([C:25]4[CH:30]=[CH:29][C:28]([F:31])=[C:27]([C:32]([F:35])([F:33])[F:34])[CH:26]=4)[N:24]=3)=[O:18])[C:6]=2[C:5](=[O:12])[N:4]([CH3:13])[C:3]1=[O:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66742610HCID 66742610, compoundHCID 86662182HCID 86662182, compound

Product 1

HCID 46947247HCID 46947247, 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-(4-fluoro-3-trifluoromethylphenyl)-1,3-thiazol-2-yl]acetamide (128 mg, 0.334 mmol) in the presence of NaH (16 mg, 0.666 mmol) in dry DMF (5.0 mL) to give 75 mg of the product as an off-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), 7.36 (s, 1H), 7.58-7.66 (m, 1H), 7.88 (s, 1H), 8.24-8.32 (m, 2H), 12.74 (br s, 1H); APCI-MS (m/z) 480.16 (M−H).

Sources & evidence

ORD record
ord-95acf8f4461e42499d1164252248baec
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

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