Sodium hydride → HCID 46945045, compound

HRID 467870Notes

Reaction equation

HRID 467870 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]=[CH:30][C:29]([O:32][CH2:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[C:28]([Cl:38])[CH:27]=2)[N:25]=1)=[O:19].[H-].[Na+]>CN(C=O)C>[Cl:38][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]=[CH:30][C:29]=1[O:32][CH2:33][C:34]([CH3:37])([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 53675961HCID 53675961, compoundHCID 86762212HCID 86762212, compound

Product 1

HCID 46945045HCID 46945045, 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-[3-chloro-4-(2,2-dimethylpropoxy)phenyl]-1,3-thiazol-2-yl}acetamide (129 mg, 0.308 mmol) in the presence of NaH (15 mg, 0.375 mmol) in dry DMF (5.0 mL) to give 85 mg of the product as a white solid; 1H-NMR (δ ppm, DMSO-d6, 300 MHz): 1.04 (s, 9H), 2.27 (s, 3H), 3.17 (s, 3H), 3.36 (s, 3H), 3.76 (s, 2H), 5.32 (s, 2H), 6.07 (s, 1H), 7.19 (d, J=8.7 Hz, 1H), 7.62 (s, 1H), 7.82 (d, J=8.4 Hz, 1H), 7.96 (s, 1H), 12.69 (br s, 1H, exchangeable with D2O); APCI-MS (m/z) 530.26 (M+H)+.

Sources & evidence

ORD record
ord-f20b5cc8ffb2487fbe1e88a9431c8eae
Source dataset
uspto-grants-2014_01
Patent number
US08623880B2

Reaction notes

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