Sodium hydride → HCID 46945046, compound

HRID 467869Notes

Reaction equation

HRID 467869 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]([F:38])[CH:27]=2)[N:25]=1)=[O:19].[H-].[Na+]>CN(C=O)C>[CH3:35][C:34]([CH3:37])([CH3:36])[CH2:33][O:32][C:29]1[CH:30]=[CH:31][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:27][C:28]=1[F:38]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 53675961HCID 53675961, compoundHCID 86762211HCID 86762211, compound

Product 1

HCID 46945046HCID 46945046, 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-[4-(2,2-dimethylpropoxy)-3-fluorophenyl]-1,3-thiazol-2-yl}acetamide (124 mg, 0.310 mmol) in the presence of NaH (15 mg, 0.375 mmol) in dry DMF (5.0 mL) to give 55 mg of the product as a white solid; 1H-NMR (δ ppm, DMSO-d6, 300 MHz) 1.06 (s, 9H), 2.26 (s, 3H), 3.17 (s, 3H), 3.36 (s, 3H), 3.75 (s, 2H), 5.32 (s, 2H), 6.07 (s, 1H), 7.22 (t, J=8.4 Hz, 1H), 7.59 (s, 1H), 7.65-7.75 (m, 2H), 12.77 (br s, 1H, exchangeable with D2O); APCI-MS (m/z) 514.16 (M+H)+.

Sources & evidence

ORD record
ord-68a0fe8b922c4d94959745f4b8614ac3
Source dataset
uspto-grants-2014_01
Patent number
US08623880B2

Reaction notes

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