Sodium hydride → HCID 69892912, compound

HRID 2121274Notes

Reaction equation

HRID 2121274 reaction equation
C[O:2][C:3](=[O:34])[C@H:4]([CH2:30][CH2:31][S:32][CH3:33])[NH:5][C:6](=[O:29])[C:7]1[CH:12]=[CH:11][C:10]([CH:13]=[CH:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][C:20]=2Cl)=[CH:9][C:8]=1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH3:28].[H-].[Na+:36]>CN(C=O)C.C(O)CC>[Na+:36].[CH2:3]([O:2][C:20]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[CH:14]=[CH:13][C:10]1[CH:11]=[CH:12][C:7]([C:6]([NH:5][C@H:4]([C:3]([O-:2])=[O:34])[CH2:30][CH2:31][S:32][CH3:33])=[O:29])=[C:8]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH3:28])[CH:9]=1)[CH2:4][CH3:30]

Participants

5

Reactant 2

HCID 24758Sodium hydrideHCID 69892484HCID 69892484, compound

Product 1

HCID 69892912HCID 69892912, compound

Reagents, catalysts & solvents 2

HCID 10311-PropanolSolventHCID 6228DimethylformamideSolvent

Procedure

N-[4-(2-(4-chloropyridin-3-yl)ethenyl)-2-(2-methylphenyl)benzoyl]methionine methyl ester, prepared as in Example 1040, (28 mg, 0.06 mmol) was dissolved in DMF (1 mL) with n-propanol (0.1 mL) and treated with NaH (60% in mineral oil, 6.8 mg, 0.17 mmol). After stirring 18 hours at ambient temperature, the reaction was evaporated and lyophilized from water to provide 29 mg of the title compound. MS m/e 505 (M+H)+. 1H NMR (d6-DMSO, 300 MHz) δ 1.03 (m, 3H), 1.24 (m, 2H), 1.6 (m, 3H), 2.0 (m, 7H), 3.71 (m, 2H), 6.94 (m, 1H), 7.3 (m, 9H), 7.74 (m, 1H), 8.33 (m, 1H), 8.52 (m, 1H), 8.67 (s, 1H).

Workup

  1. customthe reaction was evaporated

Sources & evidence

ORD record
ord-a1b324600c72400397392caec2f10127
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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