Acetic Acid → 3-Isopropylamino-pyrazole-1-carboxylic acid tert-butyl ester

HRID 1898195Notes

Reaction equation

HRID 1898195 reaction equation
[CH3:1][C:2]([CH3:4])=O.C(O)(=O)C.[C:9]([O:13][C:14]([N:16]1[CH:20]=[CH:19][C:18]([NH2:21])=[N:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:9]([O:13][C:14]([N:16]1[CH:20]=[CH:19][C:18]([NH:21][CH:2]([CH3:4])[CH3:1])=[N:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 51358380tert-Butyl 3-amino-1H-pyrazole-1-carboxylate

Product 1

HCID 579422763-Isopropylamino-pyrazole-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of acetone (0.1 mL, 1.4 mmol), acetic acid (0.078 mL, 1.43 mmol) and 3-amino-pyrazole-1-carboxylic acid tert-butyl ester (200 mg, 1.1 mmol) in DCM (5 mL) was stirred at RT for 1 hour. Sodium triacetoxyborohydride (467 mg, 2.2 mmol) was added and the mixture stirred overnight. The mixture was extracted with ethyl acetate, washed with water, dried and concentrated. The residue was purified by flash column to give 3-Isopropylamino-pyrazole-1-carboxylic acid tert-butyl ester.

Workup

  1. stirringthe mixture stirred overnight
  2. extractionThe mixture was extracted with ethyl acetate
  3. washwashed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by flash column

Sources & evidence

ORD record
ord-4c1456914cba4f99bb8b6cdaba05e366
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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