Triethylamine → 6-{(SR)-1-[(3RS,4SR)-1-(4-Cyano-piperidine-1-carbonyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile

HRID 1158667노트

반응식

HRID 1158667 반응식
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:9][CH:10]([CH:12]2[CH:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=3)[CH2:15][N:14]([C:25](Cl)=[O:26])[CH2:13]2)[CH3:11])=[N:7][CH:8]=1)#[N:2].CCN(CC)CC.[NH:35]1[CH2:40][CH2:39][CH:38]([C:41]#[N:42])[CH2:37][CH2:36]1>C(Cl)Cl>[C:41]([CH:38]1[CH2:39][CH2:40][N:35]([C:25]([N:14]2[CH2:15][CH:16]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([Cl:24])[CH:18]=3)[CH:12]([CH:10]([O:9][C:6]3[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][N:7]=3)[CH3:11])[CH2:13]2)=[O:26])[CH2:36][CH2:37]1)#[N:42]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 1382234-CyanopiperidineHCID 86628181(3RS,4SR)-3-[(SR)-1-(5-Cyano-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl chloride

생성물 1

HCID 673276916-{(SR)-1-[(3RS,4SR)-1-(4-Cyano-piperidine-1-carbonyl)-4-(3,4-dichloro-phenyl)-pyrrolidin-3-yl]-ethoxy}-nicotinonitrile수율 69%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of (3RS,4SR)-3-[(SR)-1-(5-Cyano-pyridin-2-yloxy)-ethyl]-4-(3,4-dichloro-phenyl)-pyrrolidine-1-carbonyl chloride (30 mg, 0.070 mmol) in CH2Cl2 (4 mL) were added Et3N (0.015 mL, 0.11 mmol) and piperidine-4-carbonitrile (commercially available) (9 mg, 0.084 mmol). Stirring was continued overnight, and the reaction mixture was concentrated under vacuo and directly purified by flash chromatography (SiO2, EtOAc) to yield 24 mg (69%) the title compound as light yellow oil. ES-MS m/e: 498.0 (M+H+).

후처리

  1. concentrationthe reaction mixture was concentrated under vacuo
  2. customdirectly purified by flash chromatography (SiO2, EtOAc)

출처 및 근거

ORD 기록
ord-105de65fd74d44909e7ed76bd1bb57de
출처 데이터셋
uspto-grants-2010_10
특허 번호
US07812021B2

반응 노트

불러오는 중…