Sodium hydride → HCID 86662206, compound

HRID 1467851Notes

Reaction equation

HRID 1467851 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][CH:34]3[CH2:37][CH2:36][CH2:35]3)=[C:27]([F:38])[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:26]=[C:27]([F:38])[C:28]([O:32][CH2:33][CH:34]5[CH2:37][CH2:36][CH2:35]5)=[C:29]([F:31])[CH:30]=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 86662207HCID 86662207, compound

Product 1

HCID 86662206HCID 86662206, 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-(cyclobutylmethoxy)-3,5-difluorophenyl]-1,3-thiazol-2-yl}acetamide (139 mg, 0.334 mmol) in the presence of NaH (16 mg, 0.666 mmol) in dry DMF (5.0 mL) to give 44 mg of the product as a white solid; 1H NMR (δ ppm, 300 MHz, DMSO-d6) 1.82-1.90 (m, 4H), 2.00-2.06 (m, 2H), 2.65-2.70 (m, 1H), 3.17 (s, 3H), 3.39 (s, 3H), 4.07-4.13 (m, 2H), 5.32 (s, 2H), 6.20-6.26 (m, 1H), 7.34 (s, 1H), 7.63 (d, J=8.7 Hz, 2H), 7.77 (s, 1H), 12.67 (br s, 1H); APCI-MS (m/z) 516.11 (M+H)+.

Sources & evidence

ORD record
ord-aa777b25827c46d683cecb081ea71605
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

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