5-Chloro-2-thiophenecarboxylic acid → Hydrochloric Acid

HRID 416496Notes

Reaction equation

HRID 416496 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]([CH3:26])[S:20]([CH2:23][CH2:24][NH2:25])(=[O:22])=[O:21])[CH2:15][CH2:14]1)([CH3:12])[CH3:11]>>[ClH:1].[CH:10]([N:13]1[CH2:18][CH2:17][CH:16]([N:19]([CH3:26])[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

4

Reactant 2

HCID 950485-Chloro-2-thiophenecarboxylic acidHCID 66625243HCID 66625243, compound

Product 2

HCID 313Hydrochloric AcidHCID 11990530HCID 11990530, compound

Procedure

5-Chloro-thiophene-2-carboxylic acid {2-[(1-isopropyl-piperidin-4-yl)-methyl-sulfamoyl]-ethyl}-amide was prepared by an analogous procedure as described for example 1 iii) starting from 318 mg (2 equiv.) 5-chloro-thiophene-2-carboxylic acid and 258 mg (0.98 mmol) crude 2-amino-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-methyl-amide. Final purification was achieved by preparative RP-HPLC (CH3CN/H2O gradient+0.1% TFA). After lyophilisation and transformation into its hydrochloride the title compound was obtained as a colorless, amorphous solid.

Workup

  1. custom5-Chloro-thiophene-2-carboxylic acid {2-[(1-isopropyl-piperidin-4-yl)-methyl-sulfamoyl]-ethyl}-amide was prepared by an analogous procedure
  2. customFinal purification

Sources & evidence

ORD record
ord-cb27b14c781244288e39e41fca2d2f38
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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