Isopropanol → (R)-1-(2-(2-methylthiazol-4-yl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide

HRID 77039

반응식

HRID 77039 반응식
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:25])[C@@H:11]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:2]2.[Br:26][CH2:27][C:28]([C:30]1[N:31]=[C:32]([CH3:35])[S:33][CH:34]=1)=[O:29].CC(O)C>C(#N)C>[Br-:26].[CH3:35][C:32]1[S:33][CH:34]=[C:30]([C:28](=[O:29])[CH2:27][N+:1]23[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]2)[C@@H:3]([O:9][C:10](=[O:25])[C@@H:11]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:2]3)[N:31]=1

참가 물질

5

반응물 3

HCID 3776IsopropanolHCID 128711692-Bromo-1-(2-methylthiazol-4-yl)ethanoneHCID 46840261(R)-((R)-quinuclidin-3-yl) 2-phenyl-2-(phenylamino)acetate

생성물 1

HCID 86643226(R)-1-(2-(2-methylthiazol-4-yl)-2-oxoethyl)-3-((R)-2-phenyl-2-(phenylamino)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide수율 35.4%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

(R)-Phenyl-phenylamino-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (Diastereoisomer 1 of C2) (75.0 mg, 0.22 mmol) and 2-bromo-1-(2-methylthiazol-4-yl)ethanone (I228) (49.1 mg, 0.22 mmol) in acetonitrile (5 mL) is heated at 100° C. for 75 minutes under microwave irradiation (UPLC-MS monitoring: complete conversion). The solvent is removed and the resulting brown solid is tritured with iPr2O/Et2O (1/1) and then with iPrOH to obtain the title compound as a grey powder (43.3 mg, 35% yield, bromide salt, single diastereoisomers).

후처리

  1. customThe solvent is removed

출처 및 근거

ORD 기록
ord-6d2ea4ca003e43ada78c8affd660dfcc
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08835682B2

연결된 노트

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