Dicyclohexylcarbodiimide → N-[(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-yl)-acetyl]-methanesulfonamide

HRID 11679

반응식

HRID 11679 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:28][C:29]([OH:31])=O)[C:5]([O:8][CH2:9][C:10]([N:12]2[CH2:17][C@H:16]([CH3:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:14][C@H:13]2[CH3:27])=[O:11])=[N:6][CH:7]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:47][S:48]([NH2:51])(=[O:50])=[O:49]>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:28][C:29]([NH:51][S:48]([CH3:47])(=[O:50])=[O:49])=[O:31])[C:5]([O:8][CH2:9][C:10]([N:12]2[CH2:17][C@H:16]([CH3:18])[N:15]([CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:14][C@H:13]2[CH3:27])=[O:11])=[N:6][CH:7]=1

참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 72879MethanesulfonamideHCID 69655717(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-yl)-acetic acid

생성물 1

HCID 69655650N-[(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-yl)-acetyl]-methanesulfonamide수율 70.2%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of N-[(5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-pyridin-3-yl)-acetic acid (0.045 g, 0.10 mmol) in dichloromethane (2 mL) was added 4-dimethylaminopyridine (0.018 g, 0.15 mmol), and 1,3-dicyclohexylcarbodiimide (0.023 g, 0.11 mmol). The resulting reaction mixture was stirred at ambient temperature for 20 minutes, and then treated with methanesulfonamide (0.011 g, 0.12 mmol). The reaction was stirred at ambient temperature for 18 hours, filtered through a pad of celite and the resulting filter cake was washed with dichloromethane. The combined organics were concentrated in vacuo and purified by silica gel chromatography followed by trituration with dichloromethane to give the title compound (0.037 g, LRMS: 525.3, 527.2).

후처리

  1. customThe resulting reaction mixture
  2. stirringThe reaction was stirred at ambient temperature for 18 hours
  3. filtrationfiltered through a pad of celite
  4. filtrationthe resulting filter cake
  5. washwas washed with dichloromethane
  6. concentrationThe combined organics were concentrated in vacuo
  7. custompurified by silica gel chromatography

출처 및 근거

ORD 기록
ord-27cf31e96e1e4b4f9eac0feb16c2e817
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07098212B2

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