Hydrochloric Acid → 2-(4-Chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-5-(naphthalen-2-ylsulfonylcarbamoyl)benzoic acid

HRID 528856Notes

Reaction equation

HRID 528856 reaction equation
[Cl:1][C:2]1[C:3]([C:35](=[O:45])[N:36]([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:37][CH2:38][CH2:39][CH3:40])=[N:4][N:5]([C:8]2[CH:18]=[CH:17][C:16]([C:19](=[O:34])[NH:20][S:21]([C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=3)(=[O:23])=[O:22])=[CH:15][C:9]=2[C:10]([O:12]CC)=[O:11])[C:6]=1[CH3:7].[OH-].[Na+].Cl>C1COCC1.CO>[Cl:1][C:2]1[C:3]([C:35](=[O:45])[N:36]([CH2:41][CH2:42][CH2:43][CH3:44])[CH2:37][CH2:38][CH2:39][CH3:40])=[N:4][N:5]([C:8]2[CH:18]=[CH:17][C:16]([C:19](=[O:34])[NH:20][S:21]([C:24]3[CH:33]=[CH:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=3)(=[O:22])=[O:23])=[CH:15][C:9]=2[C:10]([OH:12])=[O:11])[C:6]=1[CH3:7]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 71062150ethyl 2-(4-chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-5-(naphthalen-2-ylsulfonylcarbamoyl)benzoate

Product 1

HCID 710621452-(4-Chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-5-(naphthalen-2-ylsulfonylcarbamoyl)benzoic acidYield 78.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To ethyl 2-(4-chloro-3-(dibutylcarbamoyl)-5-methyl-1H-pyrazol-1-yl)-5-(naphthalen-2-ylsulfonylcarbamoyl)benzoate (1.39 g, 2.13 mmol) in THF (12.0 mL) and MeOH (4.0 mL) was added 0.5N aq. NaOH solution (21.3 mL, 10.7 mmol). The resulting reaction mixture was stirred at room temperature for 1.5 h. The mixture was then neutralized with 1N aq. HCl solution (pH=7) and extracted with EtOAc (3×). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo. The crude oil was triturated with CH2Cl2 (3×) to give the title compound (1.04 g, 78%) as a white solid. 1H NMR (DMSO-d6) δ 13.36 (br s, 1H), 8.71 (s, 1H), 8.43 (d, J=2.0 Hz, 1H), 8.26 (d, J=8.1 Hz, 1H), 8.17 (dd, J=8.4, 2.2 Hz, 2H), 8.07 (d, J=8.1 Hz, 1H), 7.99 (dd, J=8.7, 1.9 Hz, 1H), 7.78-7.64 (m, 3H), 3.38 (t, J=7.4 Hz, 2H), 3.29 (t, J=7.4 Hz, 2H), 2.10 (s, 3H), 1.58-1.38 (m, 4H), 1.36-1.22 (m, 2H), 1.13 (dq, J=14.8, 7.4 Hz, 2H), 0.90 (t, J=7.4 Hz, 3H), 0.74 (t, J=7.4 Hz, 3H); MS(ESI+) m/z 625.2 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with EtOAc (3×)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude oil was triturated with CH2Cl2 (3×)

Sources & evidence

ORD record
ord-09cf43d619374adb89fc9044998cd23b
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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