5-Bromo-2-furanecarboxylic acid → HCID 66624466, compound

HRID 416505Notes

Reaction equation

HRID 416505 reaction equation
[Br:1][C:2]1[O: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][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]([NH:19][S:20]([CH2:23][CH2:24][NH:25][C:7]([C:5]2[O:6][C:2]([Br: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 685115-Bromo-2-furanecarboxylic acidHCID 666246312-Amino-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-amide

Product 1

HCID 66624466HCID 66624466, compound

Procedure

5-Bromo-furan-2-carboxylic acid [2-(1-isopropyl-piperidin-4-ylsulfamoyl)-ethyl]-amide was prepared by an analogous procedure as described in example 9 starting from 126 mg (1.1 equiv.) 5-bromo-furan-2-carboxylic acid and 150 mg (0.60 mmol) 2-amino-ethanesulfonic acid (1-isopropyl-piperidin-4-yl)-amide. Final purification by preparative RP-HPLC (CH3CN/H2O gradient+0.1% TFA) gave pure 5-bromo-furan-2-carboxylic acid [2-(1-isopropyl-piperidin-4-ylsulfamoyl)-ethyl]-amide. The title compound was obtained as its trifluoroacetate in form of a colorless amorphous material. Yield: 121 mg MS (ES+): m/e=422, bromo pattern.

Workup

  1. custom5-Bromo-furan-2-carboxylic acid [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-b3c601015835426892a29739cf8d5860
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

Loading…