1-Benzyl 3-ethyl 4-(4-chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)isophthalate → 4-(4-Chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-3-(ethoxycarbonyl)benzoic acid

HRID 528855Notes

Reaction equation

HRID 528855 reaction equation
[Cl:1][C:2]1[C:3]([C:29](=[O:39])[N:30]([CH2:35][CH2:36][CH2:37][CH3:38])[CH2:31][CH2:32][CH2:33][CH3:34])=[N:4][N:5]([C:8]2[CH:23]=[CH:22][C:11]([C:12]([O:14]CC3C=CC=CC=3)=[O:13])=[CH:10][C:9]=2[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:6]=1[CH3:7]>CO.[Pd]>[Cl:1][C:2]1[C:3]([C:29](=[O:39])[N:30]([CH2:35][CH2:36][CH2:37][CH3:38])[CH2:31][CH2:32][CH2:33][CH3:34])=[N:4][N:5]([C:8]2[CH:23]=[CH:22][C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]=2[C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:6]=1[CH3:7]

Participants

4

Reactant 1

HCID 710625421-Benzyl 3-ethyl 4-(4-chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)isophthalate

Product 1

HCID 710621684-(4-Chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-3-(ethoxycarbonyl)benzoic acidYield 85%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a 30 mL pressure flask containing 10% Pd/C (59 mg, 0.055 mmol) was added a solution of 1-benzyl 3-ethyl 4-(4-chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)isophthalate (153 mg, 0.28 mmol) in MeOH (5.0 mL). The reaction mixture was stirred under H2 at 5 psi for 1 h, then filtered through a pipette containing a plug of CELITE® and concentrated in vacuo to give the title compound (110 mg, 85%) as a colorless oil. 1H NMR (CDCl3) δ 8.72 (d, J=2.0 Hz, 1H), 8.35 (dd, J=8.1, 2.0 Hz, 1H), 7.49 (d, J=8.1 Hz, 1H), 4.21 (q, J=7.3 Hz, 2H), 3.56-3.49 (m, 2H), 3.46-3.38 (m, 2H), 2.20-2.13 (m, 3H), 1.71-1.60 (m, 2H), 1.59-1.50 (m, 1H), 1.47-1.33 (m, 2H), 1.30-1.15 (m, 5H), 0.96 (t, J=7.3 Hz, 3H), 0.83 (t, J=7.4 Hz, 3H); MS(ESI+) m/z 464.2 (M+H)+.

Workup

  1. filtrationfiltered through a pipette
  2. additioncontaining a plug of CELITE®
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1f09b94486654321aa7aa78b88105f77
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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