1,2-Dichloroethane → (2S)-1-[(4-Chlorophenyl)sulfonyl]-2-methyl-4-[(6-methyl-3-pyridinyl)carbonyl]piperazine

HRID 43394

반응식

HRID 43394 반응식
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]2[CH2:17][CH2:16][NH:15][CH2:14][C@@H:13]2[CH3:18])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.[CH3:33][C:34]1[N:39]=[CH:38][C:37]([C:40](O)=[O:41])=[CH:36][CH:35]=1.C(N1CCOCC1)C>C(Cl)Cl.O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([N:12]2[CH2:17][CH2:16][N:15]([C:40]([C:37]3[CH:38]=[N:39][C:34]([CH3:33])=[CH:35][CH:36]=3)=[O:41])[CH2:14][C@@H:13]2[CH3:18])(=[O:10])=[O:11])=[CH:7][CH:8]=1

참가 물질

8

반응물 5

HCID 111,2-DichloroethaneHCID 7525EthylmorpholineHCID 757711-HydroxybenzotriazoleHCID 1378606-Methylnicotinic acidHCID 67028562(2S)-1-[(4-Chlorophenyl)sulfonyl]-2-methylpiperazine hydrochloride

생성물 1

HCID 59161398(2S)-1-[(4-Chlorophenyl)sulfonyl]-2-methyl-4-[(6-methyl-3-pyridinyl)carbonyl]piperazine수율 41.3%

시약·촉매·용매 2

HCID 962Water용매2회HCID 6344Dichloromethane용매

실험 절차

To a suspension of (2S)-1-[(4-chlorophenyl)sulfonyl]-2-methylpiperazine hydrochloride (Description 4) (105 mg, 0.338 mmol), EDC (71.2 mg, 0.371 mmol), HOBT.H2O (56.9 mg, 0.371 mmol) and 6-methyl-3-pyridinecarboxylic acid (51.0 mg, 0.372 mmol) in DCM (5 ml) was added N-ethylmorpholine (0.090 ml, 0.710 mmol). The reaction was stirred for 18 h at ambient temperature. To the reaction was added water (3 ml) and the organic layer collected via a hydrophobic frit. The organic layer was reduced in volume to approximately 2 ml then loaded onto a silica SP4 chromatography cartridge. The cartridge was eluted with ethyl acetate then a gradient from 0-10% (20% methanol in dichloromethane) in ethyl. Fractions containing the desired product were combined and reduced in vacuo to yield the title compound as a white solid (55 mg).

후처리

  1. customthe organic layer collected via a hydrophobic frit
  2. washThe cartridge was eluted with ethyl acetate
  3. additionFractions containing the desired product

출처 및 근거

ORD 기록
ord-5ea037a08ea043bf8ede033f0ff8dad6
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536183B2

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