5-Chloro-2-thiophenecarboxylic acid → HCID 66625064, compound

HRID 416503Notes

Reaction equation

HRID 416503 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([OH:9])=O)=[CH:4][CH:3]=1.[CH2:10]([N:17]1[CH2:22][CH2:21][N:20]([NH:23][S:24]([CH2:27][CH2:28][NH2:29])(=[O:26])=[O:25])[CH2:19][CH2:18]1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>>[CH2:10]([N:17]1[CH2:18][CH2:19][N:20]([NH:23][S:24]([CH2:27][CH2:28][NH:29][C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:9])(=[O:26])=[O:25])[CH2:21][CH2:22]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

3

Reactant 2

HCID 950485-Chloro-2-thiophenecarboxylic acidHCID 66624719HCID 66624719, compound

Product 1

HCID 66625064HCID 66625064, compound

Procedure

5-Chloro-thiophene-2-carboxylic acid [2-(4-benzyl-piperazin-1-ylsulfamoyl)-ethyl]-amide was prepared by an analogous procedure as described in example 5 iii) starting from 100 mg (1 equiv.) 5-chloro-thiophene-2-carboxylic acid and 183 mg (0.61 mmol) 2-amino-ethanesulfonic acid (4-benzyl-piperazin-1-yl)-amide. Final purification by preparative RP-HPLC (CH3CN/H2O gradient+0.1% TFA) gave pure 5-chloro-thiophene-2-carboxylic acid [2-(4-benzyl-piperazin-1-ylsulfamoyl)-ethyl]-amide. The title compound was obtained as its trifluoroacetate in form of a colorless amorphous material. Yield: 41 mg

Workup

  1. custom5-Chloro-thiophene-2-carboxylic acid [2-(4-benzyl-piperazin-1-ylsulfamoyl)-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-84a83110e24944e4bc2f6d3511f8d154
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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