Glyoxylic Acid → 2-(5-(trifluoromethyl)-1H-indazol-3-ylamino)acetic acid

HRID 2089243Notes

Reaction equation

HRID 2089243 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[NH2:12].O=[CH:16][C:17]([OH:19])=[O:18].[BH3-]C#N.[Na+]>CO>[F:14][C:2]([F:1])([F:13])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[NH:12][CH2:16][C:17]([OH:19])=[O:18]

Participants

5

Reactant 3

HCID 760Glyoxylic AcidHCID 16736Bay-H-1127HCID 5003444Sodium cyanoborohydride

Product 1

HCID 219911872-(5-(trifluoromethyl)-1H-indazol-3-ylamino)acetic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of 5-(trifluoromethyl)-1H-indazol-3-amine (as prepared in the previous step, 50 mg, 0.25 mmol, 1.00 equiv) in MeOH (10 mL), 2-oxoacetic acid (80% in water) (27.6 mg, 0.37 mmol, 1.20 equiv) and NaBH3CN (105 mg, 0.50 mmol, 2.00 equiv). The reaction mixture was stirred for 2 h at room temperature, then concentrated under vacuum to give 2-(5-(trifluoromethyl)-1H-indazol-3-ylamino)acetic acid as a yellow solid. LC-MS-(ES, m/z) 261[M+H]+

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-be24a170ba7640b1be6d653413fc3c39
Source dataset
uspto-grants-2013_05
Patent number
US08436023B2

Reaction notes

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