Acetic Acid → HCID 59146141, compound

HRID 1512788Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[N:24]([CH3:26])[CH:23]=[C:22]4[CH:27]=O)[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:11])[CH3:10].[NH2:29][C@H:30]([C:32]([O:34][CH3:35])=[O:33])[CH3:31].C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([C:12]2[O:16][N:15]=[C:14]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]4[C:25]=3[N:24]([CH3:26])[CH:23]=[C:22]4[CH2:27][NH:29][C@H:30]([C:32]([O:34][CH3:35])=[O:33])[CH3:31])[N:13]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH:9]([CH3:10])[CH3:11]

Participants

Conditions

Temperature: 35 °C

Procedure

To a stirred solution of 7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indole-3-carbaldehyde (D61) (395 mg), methyl L-alaninate (206 mg) and acetic acid (60 mg) in DCM (10 mL) was added NaBH(OAc)3 (424 mg). The mixture was stirred at 35° C. overnight. After cooled to room temperature, the reaction mixture was diluted with DCM (10 mL), washed with water and saturated sodium bicarbonate solution. The organic phase was separated and dried over anhydrous sodium sulphate. The solvent was evaporated and the residue was purified by Mass Directed Auto Prep to afford methyl N-{[7-(5-{3-chloro-4-[(1-methylethyl)oxy]phenyl}-1,2,4-oxadiazol-3-yl)-1-methyl-1H-indol-3-yl]methyl}-L-alaninate (D81) as a white solid (160 mg). MS (ES): C26H27ClN4O4 requires 482; found 380.1 (M—C4H8NO2+).

Workup

temperatureAfter cooled to room temperature
washwashed with water and saturated sodium bicarbonate solution
customThe organic phase was separated
dry with materialdried over anhydrous sodium sulphate
customThe solvent was evaporated
customthe residue was purified by Mass Directed Auto Prep

Sources & evidence

ORD record: ord-2658a63fa6fa471286d7e550507f4550
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08217028B2

Reaction notes

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