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

HRID 2225209Notes

Reaction equation

HRID 2225209 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[NH:12][CH2:13][C:14]([O:16]CC)=[O:15].[Li+].[OH-].CO.Cl>C1COCC1>[F:20][C:2]([F:1])([F:19])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[C:6]2[NH:12][CH2:13][C:14]([OH:16])=[O:15]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 68469013ethyl 2-(5-(trifluoromethyl)-1H-indazol-3-ylamino)acetate

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Preparation I6, Step 3: A sample of ethyl 2-(5-(trifluoromethyl)-1H-indazol-3-ylamino)acetate (75 mg) was dissolved in THF (6 mL). The resulting solution was charged successively with an aqueous solution of LiOH (12.5 mg in 2 mL water) and methanol (2 mL). The reaction mixture was stirred for 2 h before being acidified with 1N HCl and extracted with EtOAc. The organic extracts were combined, washed with water and brine, dried (sodium sulfate), filtered, and concentrated under reduced pressure to afford 2-(5-(trifluoromethyl)-1H-indazol-3-ylamino)acetic acid. MS found: (M+H)+=260.22.

Workup

  1. customPreparation I6, Step 3
  2. extractionextracted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5b28191dd484457ca1b791e613ed416a
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

Loading…