Hydrochloric Acid → HCID 19783205, compound

HRID 257560Notes

Reaction equation

HRID 257560 reaction equation
[CH2:1]([C:5]1[C:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[S:23](=[O:35])(=[O:34])[NH:24][C:25](=[O:33])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:32])=[CH:13][CH:12]=2)=[C:8]([C:36]([O:38]CC)=[O:37])[N:7]([C:41]2[CH:46]=[C:45]([NH:47][C:48](=[O:53])[CH2:49][CH2:50][CH2:51][CH3:52])[CH:44]=[CH:43][C:42]=2[Cl:54])[N:6]=1)[CH2:2][CH2:3][CH3:4].[OH-].[Na+].CO.Cl>O>[CH2:1]([C:5]1[C:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[S:23](=[O:35])(=[O:34])[NH:24][C:25](=[O:33])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:32])=[CH:13][CH:12]=2)=[C:8]([C:36]([OH:38])=[O:37])[N:7]([C:41]2[CH:46]=[C:45]([NH:47][C:48](=[O:53])[CH2:49][CH2:50][CH2:51][CH3:52])[CH:44]=[CH:43][C:42]=2[Cl:54])[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 19783157HCID 19783157, compound

Product 1

HCID 19783205HCID 19783205, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 39.5 mg (0.05 mmol) of ethyl 3-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-1-[2-chloro-5-(valerylamino)phenyl]-1H-pyrazole-5-carboxylate (from Example 1), 200 μL (0.5 mmol) of 2.5N NaOH, and 600 μL of methanol was stirred under N2 at 60° C. for 2 hours. The solution was cooled, diluted with 5 mL of H2O, and adjusted to approximately pH 2 by gradual addition of 2N HCl, resulting in precipitation. The precipitate was collected on a filter and dried to yield 37.8 mg (97%) of the title compound as a nearly white solid, mp>110° C. (gradual); homogeneous by TLC in 9:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 761 (M+1)+. 400 MHz 1H NMR (DMSO-d6) δ0.80 (t, J=7.3 Hz, 3H), 0.88, (t, J=7.3 Hz, 3H), 1.24, 1.31 (overlapping m, each 2H), 1.47 (m, 2H), 1.57 (m, 2H), 2.31 (t, J=7.4 Hz, 2H), 2.48 (t, 2H, partially obscured by DMSO peak), 4.18 (br, 2H), 7.09 (d, J=7.4 Hz, 1H), 7.21 (d, J=8.3 Hz, 2H), 7.27-7.74 (m, 10H), 7.87 (d, J=2.5 Hz, 1H), 8.17 (dd, J=8.0, 1.3 Hz, 1H).

Workup

  1. temperatureThe solution was cooled
  2. customresulting in precipitation
  3. customThe precipitate was collected on
  4. filtrationa filter
  5. customdried

Sources & evidence

ORD record
ord-9b324719b5424fbda6a9ec41ca97d6bb
Source dataset
uspto-grants-1993_11
Patent number
US05262412

Reaction notes

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