5-Chloro-2-thiophenecarboxylic acid → HCID 66624916, compound

HRID 416532Notes

Reaction equation

HRID 416532 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.[CH:10]([N:13]1[CH2:18][CH2:17][CH:16]([NH:19][S:20]([CH2:23][C:24]([NH2:27])([CH3:26])[CH3:25])(=[O:22])=[O:21])[CH2:15][CH2:14]1)([CH3:12])[CH3:11]>>[CH:10]([N:13]1[CH2:18][CH2:17][CH:16]([NH:19][S:20]([CH2:23][C:24]([NH:27][C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:9])([CH3:25])[CH3:26])(=[O:22])=[O:21])[CH2:15][CH2:14]1)([CH3:12])[CH3:11]

Participants

3

Reactant 2

HCID 950485-Chloro-2-thiophenecarboxylic acidHCID 66624635HCID 66624635, compound

Product 1

HCID 66624916HCID 66624916, compound

Procedure

5-Chloro-thiophene-2-carboxylic acid [2-(1-isopropyl-piperidin-4-ylsulfamoyl)-1,1-dimethyl-ethyl]-amide was prepared by an analogous procedure as described in example 26 viii) starting from 195 mg (1 equiv.) 5-chloro-thiophene-2-carboxylic acid and 332 mg (1.2 mmol) 2-amino-2-methyl-propane-1-sulfonicacid (1-isopropyl-piperidin-4-yl)-amide. Final purification by preparative RP-HPLC (CH3CN/H2O gradient+0.1% TFA) gave pure 5-chloro-thiophene-2-carboxylic acid [2-(1-isopropyl-piperidin-4-ylsulfamoyl)-1,1-dimethyl-ethyl]-amide. The title compound was obtained as its trifluoroacetate in form of a colorless amorphous material.

Workup

  1. custom5-Chloro-thiophene-2-carboxylic acid [2-(1-isopropyl-piperidin-4-ylsulfamoyl)-1,1-dimethyl-ethyl]-amide was prepared by an analogous procedure
  2. customFinal purification by preparative RP-HPLC (CH3CN/H2O gradient+0.1% TFA)

Sources & evidence

ORD record
ord-e5623d205b6d4e44a9c3e513fbfa1018
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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