Ethyl Acetate → 4-(3-Tert-butyl-5-phenoxycarbonylamino-pyrazol-1-yl)benzoic acid methyl ester

HRID 221861Notes

Reaction equation

HRID 221861 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([N:10]2[C:14]([NH2:15])=[CH:13][C:12]([C:16]([CH3:19])([CH3:18])[CH3:17])=[N:11]2)=[CH:6][CH:5]=1.Cl[C:22]([O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:23].C(=O)([O-])[O-].[Na+].[Na+].C(OCC)(=O)C>C1COCC1>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:5]=[CH:6][C:7]([N:10]2[C:14]([NH:15][C:22]([O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:23])=[CH:13][C:12]([C:16]([CH3:17])([CH3:19])[CH3:18])=[N:11]2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 10340Sodium Carbonate2×HCID 15891Phenyl chloroformateHCID 2973426methyl 4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)benzoate

Product 1

HCID 536301854-(3-Tert-butyl-5-phenoxycarbonylamino-pyrazol-1-yl)benzoic acid methyl esterYield 56.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(5-amino-3-tert-butyl-pyrazol-1-yl)-benzoic acid methyl ester (5.3 g, 19.4 mmol) in anhydrous THF (200 mL) was slowly added phenyl chloroformate (6.81 mL, 54.3 mmol), followed by sodium carbonate (2.1 g, 19.4 mmol). The mixture was stirred at room temperature overnight. Ethyl acetate (500 mL) was added, followed by saturated sodium carbonate (300 mL). The organic layer was washed with saturated sodium carbonate (3×) and brine (1×), dried over MgSO4, and concentrated at reduced pressure. The residue was washed with ether to give 4.3 g (56%) of the desired product. 1H-NMR (DMSO-d6) δ 10.19 (s, 1H), 8.10 (d, J=9.0 Hz, 2H), 7.73 (d, J=9.0 Hz, 2H), 7.38-7.11 (m, 5H), 6.41 (s, 1H), 3.87 (s, 3H), 1.27 (s, 1H); MS LC-MS [M+H]+=394.1, RT=3.53 min.

Workup

  1. washThe organic layer was washed with saturated sodium carbonate (3×) and brine (1×)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated at reduced pressure
  4. washThe residue was washed with ether

Sources & evidence

ORD record
ord-11ec3c52e167465dab592d955791364f
Source dataset
uspto-grants-2012_06
Patent number
US08207166B2

Reaction notes

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