Sodium hydride → HCID 86662191, compound

HRID 1467843Notes

Reaction equation

HRID 1467843 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][CH:33]([F:35])[F:34])=[C:27]([F:36])[CH:26]=2)[N:24]=1)=[O:18].[H-].[Na+]>CN(C=O)C>[F:35][CH:33]([F:34])[O:32][C:28]1[C:29]([F:31])=[CH:30][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:26][C:27]=1[F:36]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 66742610HCID 66742610, compoundHCID 86662192HCID 86662192, compound

Product 1

HCID 86662191HCID 86662191, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the general procedure (Method A) by coupling Intermediate 1 (45 mg, 0.251 mmol) with 2-bromo-N-{4-[4-(difluoromethoxy)-3,5-difluorophenyl]-1,3-thiazol-2-yl}acetamide (125 mg, 0.313 mmol) in the presence of NaH (16 mg, 0.666 mmol) in dry DMF (5.0 mL) to give 20 mg of the product as an off-white solid; 1H NMR (δ ppm, DMSO-d6, 300 MHz) 3.17 (s, 3H), 3.39 (s, 3H), 5.32 (s, 2H), 6.23 (s, 1H), 7.28 (t, J=72.3 Hz, 1H), 7.35 (s, 1H), 7.79 (d, J=9.6 Hz, 2H), 7.90 (s, 1H), 12.73 (br s, 1H); ESI-MS (m/z) 498.08 (M+H)+.

Sources & evidence

ORD record
ord-55695ca4e2cf415eb613c18ac822e8c1
Source dataset
uspto-grants-2015_04
Patent number
US09000159B2

Reaction notes

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