Acetic Acid → HCID 89851602, compound

HRID 1746921Notes

Reaction equation

HRID 1746921 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

4

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 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.

Workup

  1. concentrationThe mixture was concentrated
  2. addition20 mL of water, 10 mL NaHCO3-solution and 20 mL of dichloromethane added
  3. customthe organic layer separated
  4. washwashed 2× with water
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d4bcbe0dd45842dbb4a128bc4bcf7b8d
Source dataset
uspto-grants-2015_10
Patent number
US09150545B2

Reaction notes

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