Triethylamine → [3-(5-Amino-3-tert-butyl-pyrazol-1-yl)-phenyl]-methanol

HRID 1402141Notes

Reaction equation

HRID 1402141 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N:11]2[C:15]([NH2:16])=[CH:14][C:13]([C:17]([CH3:20])([CH3:19])[CH3:18])=[N:12]2)[CH:6]=1)C.CCN(CC)CC.[BH4-].[Na+]>CCO.O>[NH2:16][C:15]1[N:11]([C:7]2[CH:6]=[C:5]([CH2:4][OH:3])[CH:10]=[CH:9][CH:8]=2)[N:12]=[C:13]([C:17]([CH3:20])([CH3:19])[CH3:18])[CH:14]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 4311764Sodium borohydride3×HCID 21867322ethyl 3-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoate

Product 1

HCID 21867318[3-(5-Amino-3-tert-butyl-pyrazol-1-yl)-phenyl]-methanolYield 87%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of Intermediate 29a (1.00 g, 3.48 mmol) and Et3N (265 μL, 1.91 mmol) in EtOH (35 mL) was added NaBH4 (198 mg, 5.23 mmol) and the suspension stirred at RT for 1.5 h. NaBH4 (198 mg, 5.23 mmol) was added and the suspension stirred for a further 19 h. NaBH4 (1.31 g, 34.8 mmol) was added and the suspension stirred for a further 24 h, then diluted with water and extracted with DCM. The combined organics were dried and concentrated in vacuo. The residue was purified by FCC, using 0-10% [2M NH3 in MeOH] in DCM, to give the title compound as a white solid (740 mg, 87%). LCMS (Method 3): Rt 2.05 min, m/z 246 [MH+].

Workup

  1. stirringthe suspension stirred for a further 19 h
  2. stirringthe suspension stirred for a further 24 h
  3. extractionextracted with DCM
  4. customThe combined organics were dried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by FCC

Sources & evidence

ORD record
ord-3f684ee64dae47d8bbf3e55f319ff331
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

Loading…