Sodium hydride → HCID 86762210, compound

HRID 467868Notes

Reaction equation

HRID 467868 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]=[C:30]([F:32])[C:29]([O:33][CH2:34][CH:35]3[CH2:38][CH2:37][CH2:36]3)=[C:28]([F:39])[CH:27]=2)[N:25]=1)=[O:19].[H-].[Na+]>CN(C=O)C>[CH:35]1([CH2:34][O:33][C:29]2[C:30]([F:32])=[CH:31][C:26]([C:24]3[N:25]=[C:21]([NH:20][C:18](=[O:19])[CH2:17][N:25]4[C:9]5[C:8](=[O:12])[N:7]([CH3:13])[C:6](=[O:14])[N:5]([CH3:15])[C:4]=5[CH:23]=[C:24]4[CH3:26])[S:22][CH:23]=3)=[CH:27][C:28]=2[F:39])[CH2:38][CH2:37][CH2:36]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 53675961HCID 53675961, compoundHCID 86662207HCID 86662207, compound

Product 1

HCID 86762210HCID 86762210, 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-Cyclobutylmethoxy-3,5-difluorophenyl]-1,3-thiazol-2-yl}acetamide (129 mg, 0.308 mmol) in the presence of NaH (16 mg, 0.375 mmol) in dry DMF (5.0 mL) to give 65 mg of the product as an off-white solid; 1H NMR (δ ppm, 300 MHz, DMSO-d6) 1.82-1.88 (m, 4H), 2.00-2.06 (m, 2H), 2.26 (s, 3H), 2.65-2.70 (m, 1H), 3.17 (s, 3H), 3.33 (s, 3H), 4.10 (d, J=6.6 Hz, 2H), 5.33 (s, 2H), 6.06 (s, 1H), 7.63 (d, J=8.7 Hz, 2H), 7.77 (s, 1H), 12.71 (br s, 1H); APCI-MS (m/z) 530.16 (M+H)+.

Sources & evidence

ORD record
ord-8023676c0b1745f1bb9fdaf208e0622f
Source dataset
uspto-grants-2014_01
Patent number
US08623880B2

Reaction notes

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