Sodium hydride → HCID 46947436, compound

HRID 1467842Notes

Reaction equation

HRID 1467842 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]=[C:29]([F:31])[C:28]([O:32][CH2:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[C:27]([F:38])[CH:26]=2)[N:24]=1)=[O:18].[H-].[Na+]>CN(C=O)C>[CH3:35][C:34]([CH3:37])([CH3:36])[CH2:33][O:32][C:28]1[C:29]([F:31])=[CH:30][C:25]([C:23]2[N:24]=[C:20]([NH:19][C:17](=[O:18])[CH2:16][N:10]3[C:6]4[C:5](=[O:12])[N:4]([CH3:13])[C:3](=[O:14])[N:2]([CH3:1])[C:7]=4[CH:8]=[CH:9]3)[S:21][CH:22]=2)=[CH:26][C:27]=1[F:38]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66742610HCID 66742610, compoundHCID 86662190HCID 86662190, compound

Product 1

HCID 46947436HCID 46947436, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the general procedure (Method A) by coupling Intermediate 1 (25 mg, 0.139 mmol) with 2-bromo-N-{4-[4-(2,2-dimethylpropoxy)-3,5-difluorophenyl]-1,3-thiazol-2-yl}acetamide (70 mg, 0.167 mmol) in the presence of NaH (8 mg, 0.333 mmol) in dry DMF (5.0 mL) to give 29 mg of the product as an off-white solid; 1H NMR (δ ppm, DMSO-d6, 300 MHz) 1.01 (s, 9H), 3.17 (s, 3H), 3.39 (s, 3H), 3.81 (s, 2H), 5.32 (s, 2H), 6.23 (s, 1H), 7.35 (s, 1H), 7.63 (s, 1H), 7.67 (s, 1H), 7.77 (s, 1H), 12.68 (br s, 1H); APCI-MS (m/z) 518.10 [M+H]+.

Sources & evidence

ORD record
ord-04af253512504314b916adf39e2903c3
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

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