Glyoxylic Acid → HCID 67478798, compound

HRID 2089247Notes

Reaction equation

HRID 2089247 reaction equation
[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=[C:5]2[C:4]([NH2:15])=[N:3]1.O=[CH:17][C:18]([OH:20])=[O:19].[BH3-]C#N.[Na+]>CO>[CH3:1][N:2]1[C:6]2=[N:7][CH:8]=[C:9]([C:11]([F:14])([F:12])[F:13])[CH:10]=[C:5]2[C:4]([NH:15][CH2:17][C:18]([OH:20])=[O:19])=[N:3]1

Participants

5

Reactant 3

HCID 760Glyoxylic AcidHCID 5003444Sodium cyanoborohydrideHCID 674788461-Methyl-5-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-3-amine

Product 1

HCID 67478798HCID 67478798, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of 1-methyl-5-(trifluoromethyl)-1H-pyrazolo[3,4-b]pyridin-3-amine (as prepared in the previous step, 284 mg, 1.31 mmol) in MeOH (20 mL), 2-oxoacetic acid (184 mg, 1.577 mmol) and NaBH3CN (86 mg, 1.37 mmol). The reaction mixture was stirred for 2 h at room temperature. The resulting mixture was concentrated under vacuum. After flash chromatography (silica gel, ethyl acetate) the title compound was isolated as a yellow solid.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-eca053ede7114b8db7b68cce1f4c8d6b
Source dataset
uspto-grants-2013_05
Patent number
US08436023B2

Reaction notes

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