Sodium hydride → HCID 46944850, compound

HRID 1467854Notes

Reaction equation

HRID 1467854 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]=[CH:29][C:28]([O:31][CH2:32][C:33]([F:36])([F:35])[F:34])=[C:27]([Br:37])[CH:26]=2)[N:24]=1)=[O:18].[H-].[Na+]>CN(C=O)C>[Br:37][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]=[CH:29][C:28]=1[O:31][CH2:32][C:33]([F:35])([F:34])[F:36]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66742610HCID 66742610, compoundHCID 86662212HCID 86662212, compound

Product 1

HCID 46944850HCID 46944850, 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-[3-bromo-4-(2,2,2-trifluoroethoxy)phenyl]-1,3-thiazol-2-yl}acetamide (158 mg, 0.333 mmol) in the presence of NaH (10 mg, 0.416 mmol) in dry DMF (5.0 mL) to give 30 mg of the product as a white solid; 1H NMR (δ ppm, 300 MHz, DMSO-d6) 3.17 (s, 3H), 3.39 (s, 3H), 4.91 (d, J=8.7 Hz, 2H), 5.32 (s, 2H), 6.22 (s, 1H), 7.30-7.38 (m, 2H), 7.69 (s, 1H), 7.89-7.95 (m, 1H), 8.17 (m, 1H), 12.65 (br s, 1H); APCI-MS (m/z) 572.27 (M+H)+.

Sources & evidence

ORD record
ord-468ee169deb64a079a22bddc42b2b59a
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

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