Triethylamine → HCID 54193679, compound

HRID 2271028Notes

Reaction equation

HRID 2271028 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-ea53f7a66ca74dc09b3c9ffa6d2115d7
Source dataset
uspto-grants-2001_12
Patent number
US06333324B1

Reaction notes

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