Morpholine, 4-(chloroacetyl)- → HCID 66624694, compound

HRID 416512Notes

Reaction equation

HRID 416512 reaction equation
Cl[CH2:2][C:3]([N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[CH:11]([N:14]1[CH2:19][CH2:18][CH:17]([NH:20][S:21]([CH2:24][CH2:25][NH:26][C:27]([C:29]2[S:30][C:31]([Cl:34])=[CH:32][CH:33]=2)=[O:28])(=[O:23])=[O:22])[CH2:16][CH2:15]1)([CH3:13])[CH3:12]>>[CH:11]([N:14]1[CH2:19][CH2:18][CH:17]([N:20]([CH2:2][C:3]([N:5]2[CH2:10][CH2:9][O:8][CH2:7][CH2:6]2)=[O:4])[S:21]([CH2:24][CH2:25][NH:26][C:27]([C:29]2[S:30][C:31]([Cl:34])=[CH:32][CH:33]=2)=[O:28])(=[O:22])=[O:23])[CH2:16][CH2:15]1)([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 74040Morpholine, 4-(chloroacetyl)-HCID 119904785-Chloro-Thiophene-2-Carboxylic Acid [2-(1--Isopropyl-Piperidin-4-Ylsulfamoyl)-Ethyl]-Amide

Product 1

HCID 66624694HCID 66624694, compound

Procedure

5-Chloro-thiophene-2-carboxylic acid {2-[(1-isopropyl-piperidin-4-yl)-(2-morpholin-4-yl-2-oxo-ethyl)-sulfamoyl]-ethyl}-amide was prepared by an analogous procedure as described in example 15 starting from 83 mg (2 equiv.) 2-chloro-1-morpholin-4-yl-ethanone and 100 mg (0.25 mmol) 5-chloro-thiophene-2-carboxylic acid [2-(1-isopropyl-piperidin-4-ylsulfamoyl)-ethyl]-amide. Final purification by preparative RP-HPLC (CH3CN/H2O gradient+0.1% TFA) gave pure 5-chloro-thiophene-2-carboxylic acid {2-[(1-isopropyl-piperidin-4-yl)-(2-morpholin-4-yl-2-oxo-ethyl)-sulfamoyl]-ethyl}-amide. The title compound was obtained as its trifluoroacetate in form of a colorless amorphous material, which turned out to be hygroscopic with time.

Workup

  1. custom5-Chloro-thiophene-2-carboxylic acid {2-[(1-isopropyl-piperidin-4-yl)-(2-morpholin-4-yl-2-oxo-ethyl)-sulfamoyl]-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-58655fd5eb8e4a91a1481ac05ca9762f
Source dataset
uspto-grants-2012_01
Patent number
US08088925B2

Reaction notes

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