Water → ethyl (4-[3-tert-butyl-5-[(phenoxycarbonyl)amino]-1H-pyrazol-1-yl]phenyl)acetate

HRID 221879Notes

Reaction equation

HRID 221879 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([NH2:17])=[CH:15][C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])=[N:13]2)=[CH:8][CH:7]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].Cl[C:30]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:31].O>C1COCC1.CCOC(C)=O>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]([NH:17][C:30]([O:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:31])=[CH:15][C:14]([C:18]([CH3:21])([CH3:20])[CH3:19])=[N:13]2)=[CH:8][CH:7]=1)[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 15891Phenyl chloroformateHCID 59557934ethyl [4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenyl]acetate

Product 1

HCID 59557923ethyl (4-[3-tert-butyl-5-[(phenoxycarbonyl)amino]-1H-pyrazol-1-yl]phenyl)acetateYield 76%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of ethyl[4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenyl]acetate (10 g, 33.2 mmol) and K2CO3 (9.17 g, 66.4 mmol) in THF (300 mL) was added phenyl chloroformate (8.61 mL, 66.4 mmol), and the resulting reaction mixture was stirred at room temperature overnight. The mixture was poured into a mixture of water and EtOAc and the organic phase was separated and dried over Na2SO4, concentrated at reduced pressure to afford a brown syrup, which was purified by MPLC (0% to 20% EtOAc in hexane). The desired product was obtained as a white solid (10.6 g) in 76% yield. 1H-NMR (CD2Cl2-d2) δ 7.51-7.10 (m, 10H), 6.47 (s, 1H), 4.16 (q, J=7.1 Hz, 2H), 3.71 (s, 2H), 1.37 (s, 9H), 1.28 (t, J=7.0 Hz, 3H).

Workup

  1. customthe resulting reaction mixture
  2. customthe organic phase was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated at reduced pressure
  5. customto afford a brown syrup, which
  6. customwas purified by MPLC (0% to 20% EtOAc in hexane)

Sources & evidence

ORD record
ord-072dba7c4d1b4f5a8d09e940966cd4da
Source dataset
uspto-grants-2012_06
Patent number
US08207166B2

Reaction notes

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