2-Chlorobenzoic Acid → HCID 19024433, compound

HRID 1033814Notes

Reaction equation

HRID 1033814 reaction equation
[CH2:1]([N:5]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[S:33](=[O:36])(=[O:35])[NH2:34])=[CH:23][CH:22]=1)[C:6]([N:8]([CH3:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([F:18])([F:17])[F:16])=[O:7])[CH2:2][CH2:3][CH3:4].[Cl:37][C:38]1[CH:46]=[CH:45][CH:44]=[CH:43][C:39]=1[C:40](O)=[O:41]>>[CH2:1]([N:5]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[S:33](=[O:35])(=[O:36])[NH:34][C:40](=[O:41])[C:39]2[CH:43]=[CH:44][CH:45]=[CH:46][C:38]=2[Cl:37])=[CH:25][CH:26]=1)[C:6]([N:8]([CH3:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]([F:18])([F:16])[F:17])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 83742-Chlorobenzoic AcidHCID 19024424HCID 19024424, compound

Product 1

HCID 19024433HCID 19024433, compoundYield 29%

Procedure

Following the procedure of Example 1, Step I, 1-butyl-3-methyl-1-[(2'-sulfamoylbiphenyl-4-yl)methyl]-3-[2-(trifluoromethyl)phenyl]urea was acylated with 2-chlorobenzoic acid. After work-up, the crude product was purified initially by flash chromatography on silica gel (elution with 2% and then 5% MeOH in CH2Cl2). Further purification by HPLC on a Zorbax C8 Semiprep reversed phase column (70:30 MeCN--H2O, containing 0.1% TFA) provided a 29% yield of the title compound as a stiff, white foam, mp>60° C. (gradual); homogeneous by TLC (95:5 CH2Cl2 --MeOH); FAB-MS m/e 658 (M+1)+.

Workup

  1. customAfter work-up, the crude product was purified initially by flash chromatography on silica gel (
  2. washelution with 2%
  3. customFurther purification by HPLC on a Zorbax C8 Semiprep
  4. additionphase column (70:30 MeCN--H2O, containing 0.1% TFA)

Sources & evidence

ORD record
ord-1443504921b04f85b79a86f89e43be96
Source dataset
uspto-grants-1994_05
Patent number
US05312820

Reaction notes

Loading…