5-Chloro-2-thiophenecarboxylic acid → HCID 66625006, compound

HRID 416527Notes

Reaction equation

HRID 416527 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@@H:24]([NH2:27])[CH2:25][OH:26])(=[O:22])=[O:21])[CH2:15][CH2:14]1)([CH3:12])[CH3:11]>>[OH:26][CH2:25][C@H:24]([NH:27][C:7]([C:5]1[S:6][C:2]([Cl:1])=[CH:3][CH:4]=1)=[O:9])[CH2:23][S:20](=[O:21])(=[O:22])[NH:19][CH:16]1[CH2:17][CH2:18][N:13]([CH:10]([CH3:11])[CH3:12])[CH2:14][CH2:15]1

Participants

3

Reactant 2

HCID 950485-Chloro-2-thiophenecarboxylic acidHCID 66625195HCID 66625195, compound

Product 1

HCID 66625006HCID 66625006, compound

Procedure

5-Chloro-thiophene-2-carboxylic acid [(S)-1-hydroxymethyl-2-(1-isopropyl-piperidin-4-ylsulfamoyl)-ethyl]-amide was prepared by an analogous procedure as described in example 26 viii) starting from 28 mg (1.1 equiv.) 5-chloro-thiophene-2-carboxylic acid and 44 mg (0.16 mmol) (S)-2-amino-3-hydroxy-propane-1-sulfonic acid (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 [(S)-1-hydroxymethyl-2-(1-isopropyl-piperidin-4-ylsulfamoyl)-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 [(S)-1-hydroxymethyl-2-(1-isopropyl-piperidin-4-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-c1385f7ce45a42c48fefe8538054955b
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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