Sodium borohydride → HCID 71280581, compound
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([CH:13]3[CH2:16][C:15]4([CH2:19][C:18](=[O:20])[CH2:17]4)[CH2:14]3)[O:10][N:9]=2)=[CH:4][C:3]=1[NH:21][C:22]([C:24]1[N:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]2=[N:26][CH:25]=1)=[O:23].[BH4-].[Na+]>CO>[OH:20][CH:18]1[CH2:19][C:15]2([CH2:14][CH:13]([C:11]3[O:10][N:9]=[C:8]([C:5]4[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([NH:21][C:22]([C:24]5[N:28]6[CH:29]=[CH:30][CH:31]=[CH:32][C:27]6=[N:26][CH:25]=5)=[O:23])[CH:4]=4)[N:12]=3)[CH2:16]2)[CH2:17]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirring solution of N-(2-methyl-5-(5-(6-oxospiro[3.3]heptan-2-yl)-1,2,4-oxadiazol-3-yl)phenyl)imidazo[1,2-a]pyridine-3-carboxamide (F76) (100 mg, 0.23 mmol) in anhydrous methanol (1 mL) was added sodium borohydride (10.6 mg, 0.28 mmol). The reaction mixture was stirred at room temperature for 12 hours. The reaction was quenched with water and the solvent was concentrated. Purification by silica gel using 10% MeOH in dichloromethane afforded N-(5-(5-(6-hydroxyspiro[3.3]heptan-2-yl)-1,2,4-oxadiazol-3-yl)-2-methylphenyl)imidazo[1,2-a]pyridine-3-carboxamide (F100). MS m/z 430.1 (M+1)+.