Acetic Acid → HCID 89851602, compound

Reaction equation

Cl.[NH2:2][C:3](=[O:32])[CH:4]([OH:31])[CH:5]([NH:13][C:14](=[O:30])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][C:16]=1[N:21]1[CH:29]=[C:28]2[C:23]([CH2:24][NH:25][CH2:26][CH2:27]2)=[N:22]1)[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.CO.[C:35](O)(=O)[CH3:36]>>[NH2:2][C:3](=[O:32])[CH:4]([OH:31])[CH:5]([NH:13][C:14](=[O:30])[C:15]1[CH:20]=[CH:19][CH:18]=[N:17][C:16]=1[N:21]1[CH:29]=[C:28]2[C:23]([CH2:24][N:25]([CH2:35][CH3:36])[CH2:26][CH2:27]2)=[N:22]1)[CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

Reactant 3

HCID 176Acetic Acid

HCID 887Methanol

HCID 89851640HCID 89851640, compound

Product 1

HCID 89851602HCID 89851602, compoundYield 54.3%

Procedure

To a solution of N-(4-amino-3-hydroxy-4-oxo-1-phenylbutan-2-yl)-2-(4,5,6,7-tetrahydro-2H-pyrazolo[3,4-c]pyridin-2-yl)nicotinamide hydrochloride (210 mg, 0.460 mmol) in methanol (15 ml) first acetaldehyde (150 μL, 2.66 mmol) and after 30 minutes NaCN(BH4)4 (40 mg, 0.637 mmol) and glacial acetic acid (20 μL, 0.349 mmol) were added and stirred over night. The mixture was concentrated, 20 mL of water, 10 mL NaHCO3-solution and 20 mL of dichloromethane added, the organic layer separated, washed 2× with water, dried with MgSO4, filtered and concentrated to give 85 mg of an amorphous solid; ESI-MS [M+H]+: 449.2.