5-Chloro-2-thiophenecarboxylic acid → HCID 66624479, compound

HRID 416518Notes

Reaction equation

HRID 416518 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]([N:19]([CH2:26][C:27]2[S:28][CH:29]=[CH:30][N:31]=2)[S:20]([CH2:23][CH2:24][NH2:25])(=[O:22])=[O:21])[CH2:15][CH2:14]1)([CH3:12])[CH3:11]>>[CH:10]([N:13]1[CH2:18][CH2:17][CH:16]([N:19]([CH2:26][C:27]2[S:28][CH:29]=[CH:30][N:31]=2)[S:20]([CH2:23][CH2:24][NH:25][C:7]([C:5]2[S:6][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:9])(=[O:21])=[O:22])[CH2:15][CH2:14]1)([CH3:12])[CH3:11]

Participants

3

Reactant 2

HCID 950485-Chloro-2-thiophenecarboxylic acidHCID 66625026HCID 66625026, compound

Product 1

HCID 66624479HCID 66624479, compound

Procedure

5-Chloro-thiophene-2-carboxylic acid {2-[(1-isopropyl-piperidin-4-yl)-thiazol-2-ylmethyl-sulfamoyl]-ethyl}-amide was prepared by an analogous procedure as described in example 5 iii) starting from 61 mg (1 equiv.) 5-chloro-thiophene-2-carboxylic acid and 129 mg (0.37 mmol) 2-amino-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-thiazol-2-ylmethyl-amide. Final purification by preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid) gave pure 5-chloro-thiophene-2-carboxylic acid {2-[(1-isopropyl-piperidin-4-yl)-thiazol-2-ylmethyl-sulfamoyl]-ethyl}-amide. The title compound was obtained as its formate in form of a light brown amorphous material.

Workup

  1. custom5-Chloro-thiophene-2-carboxylic acid {2-[(1-isopropyl-piperidin-4-yl)-thiazol-2-ylmethyl-sulfamoyl]-ethyl}-amide was prepared by an analogous procedure
  2. customFinal purification by preparative RP-HPLC (CH3CN/H2O gradient+0.05% formic acid)

Sources & evidence

ORD record
ord-fb38de1d64934d959ed1e459f2b8df4e
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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