Water → HCID 58662432, compound

HRID 644809Notes

Reaction equation

HRID 644809 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH:11]([CH2:12][CH3:13])[CH2:10][CH:9]([N:14]=[CH:15][C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=2)[C:8]2[C:30]([CH3:34])=[N:31][N:32]([CH3:33])[C:7]1=2)=[O:5])[CH3:2].C([BH3-])#N.[Na+].O>CO>[CH2:1]([O:3][C:4]([N:6]1[CH:11]([CH2:12][CH3:13])[CH2:10][CH:9]([NH:14][CH2:15][C:16]2[CH:17]=[C:18]([C:26]([F:27])([F:28])[F:29])[CH:19]=[C:20]([C:22]([F:24])([F:23])[F:25])[CH:21]=2)[C:8]2[C:30]([CH3:34])=[N:31][N:32]([CH3:33])[C:7]1=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 58662450HCID 58662450, compound

Product 1

HCID 58662432HCID 58662432, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of [(3,5-Bis-trifluoromethyl-benzylidene)-amino]-6-ethyl-1,3-dimethyl-1,4,5,6-tetrahydro-pyrazolo[3,4-b]pyridine-7-carboxylic acid ethyl ester (0.19 g, 0.04 mmol) obtained in step (v), in 10 mL of methanol was added sodium cyanoborohydride (0.078 g, 0.12 mmol). This reaction mixture was stirring for around 3 hours at room temperature, after which time the methanol was evaporated from the solution to afford a crude residue. Water was added to this residue, and the product was extracted with ethyl acetate (3×10 mL). The organic solvent was dried over sodium sulfate, filtered, and the solvent was evaporated from the filtrate under vacuum to provide the desired amine compound (0.019 g, 95%).

Workup

  1. customafter which time the methanol was evaporated from the solution
  2. customto afford a crude residue
  3. extractionthe product was extracted with ethyl acetate (3×10 mL)
  4. dry with materialThe organic solvent was dried over sodium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated from the filtrate under vacuum

Sources & evidence

ORD record
ord-6a9fbbba39dc4fa1ab8a3ad8cf076293
Source dataset
uspto-grants-2010_04
Patent number
US07700774B2

Reaction notes

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