Triethylamine → HCID 54193679, compound

HRID 2296677Notes

Reaction equation

HRID 2296677 reaction equation
Cl.[N:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][S:10](Cl)(=[O:12])=[O:11].[C:14]1([C:20]2[S:24][C:23]([S:25]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][C@@H:29]3[C:34]([NH:36][O:37][CH:38]3[CH2:43][CH2:42][CH2:41][CH2:40][O:39]3)=[O:35])(=[O:27])=[O:26])=[CH:22][CH:21]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[C:14]1([C:20]2[S:24][C:23]([S:25]([N:28]3[CH2:33][CH2:32][N:31]([S:10]([CH2:9][CH2:8][C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][N:2]=4)(=[O:12])=[O:11])[CH2:30][C@@H:29]3[C:34]([NH:36][O:37][CH:38]3[CH2:43][CH2:42][CH2:41][CH2:40][O:39]3)=[O:35])(=[O:26])=[O:27])=[CH:22][CH:21]=2)[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 21983734HCID 21983734, compoundHCID 54247286HCID 54247286, compound

Product 1

HCID 54193679HCID 54193679, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-(2-Pyridyl)ethanesulfonyl chloride hydrochloride (214 mg) was added to a solution of (2R)-1-(5-phenylthiophene-2-sulfonyl]-N-(2-tetrahydropyranyloxy)-2-piperazinecarboxamide (200 mg) and triethylamine (188 mg) in CHCl3 (3 ml) with cooling on an ice bath. The reaction mixture was stirred at ambient temperature for 1 hour. The mixture was concentrated in vacuo, and the residue was purified by SiO2 column chromatography eluted with MeOH in CHCl3 (1%) to give 184 mg of (2R)-1-(5-phenylthiophene-2-sulfonyl)-4-[2-(2-pyridyl)-ethanesulfonyl]-N-(2-tetrahydropyranyloxy)-2-piperazinecarboxamide as an amorphous powder.

Workup

  1. temperaturewith cooling on an ice bath
  2. concentrationThe mixture was concentrated in vacuo
  3. customthe residue was purified by SiO2 column chromatography
  4. washeluted with MeOH in CHCl3 (1%)

Sources & evidence

ORD record
ord-70c64c81985741849fe406e6e8cf58d1
Source dataset
uspto-grants-2002_12
Patent number
US06489324B2

Reaction notes

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