Sodium hydride → HCID 86662196, compound

HRID 1467846Notes

Reaction equation

HRID 1467846 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]([Cl:31])[C:28]([O:32][CH2:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[C:27]([Cl:38])[CH:26]=2)[N:24]=1)=[O:18].[H-].[Na+]>CN(C=O)C>[Cl:38][C:27]1[CH:26]=[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:30]=[C:29]([Cl:31])[C:28]=1[O:32][CH2:33][C:34]([CH3:37])([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66742610HCID 66742610, compoundHCID 86662197HCID 86662197, compound

Product 1

HCID 86662196HCID 86662196, 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, 0.110 mmol) with 2-bromo-N-{4-[3,5-dichloro-4-(2,2-dimethylpropoxy)phenyl]-1,3-thiazol-2-yl}acetamide (23 mg, 0.128 mmol) in the presence of NaH (7 mg, 0.291 mmol) in dry DMF (5.0 mL) to give 30 mg of the product as an off-white solid; 1H NMR (δ ppm, DMSO-d6, 300 MHz) 1.08 (s, 9H), 3.17 (s, 3H), 3.39 (s, 3H), 3.67 (s, 2H), 5.32 (s, 2H), 6.22 (s, 2H), 7.35 (s, 1H), 7.85 (s, 1H), 8.00 (s, 2H), 12.68 (br s, 1H); APCI-MS (m/z) 550.20 [M+H]+.

Sources & evidence

ORD record
ord-703d9d1bb3ab45bea15a5d00f9c2c652
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

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