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2-Bromo-1-(1,3-thiazol-2-yl)ethan-1-one → (R)-3-(2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiazol-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 469464
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인쇄 미리보기

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HRID 469464 반응식
[Br:1][CH2:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][N:9]=1)=[O:4].[S:10]1[CH:14]=[C:13]([CH:15]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:16]([O:18][C@@H:19]2[CH:24]3[CH2:25][CH2:26][N:21]([CH2:22][CH2:23]3)[CH2:20]2)=[O:17])[C:12]2[CH:34]=[CH:35][CH:36]=[CH:37][C:11]1=2>CCOC(C)=O>[Br-:1].[S:10]1[CH:14]=[C:13]([CH:15]([NH:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:16]([O:18][C@@H:19]2[CH:24]3[CH2:25][CH2:26][N+:21]([CH2:2][C:3](=[O:4])[C:5]4[S:6][CH:7]=[CH:8][N:9]=4)([CH2:22][CH2:23]3)[CH2:20]2)=[O:17])[C:12]2[CH:34]=[CH:35][CH:36]=[CH:37][C:11]1=2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

4

반응물 2

HCID 27952122-Bromo-1-(1,3-thiazol-2-yl)ethan-1-oneHCID 58556957(R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetate

생성물 1

HCID 54765170(R)-3-(2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiazol-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide수율 28.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

2-Bromo-1-(thiazol-2-yl)ethanone (52.5 mg, 0.25 mmol) was added portion-wise to a solution of (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetate (C19) (100 mg, 0.25 mmol) in EtOAc (2 ml). The reaction mixture was stirred at room temperature overnight. The precipitate was filtered, washed with EtOAc and purified by preparative HPLC (Eluent: CH3CN, H2O) to obtain (R)-3-(2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiazol-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide (42 mg, 27.5% yield).

후처리

  1. filtrationThe precipitate was filtered
  2. washwashed with EtOAc
  3. custompurified by preparative HPLC (Eluent: CH3CN, H2O)

출처 및 근거

ORD 기록
ord-4350582e316541b986fc4ad34d2c8bfa
출처 데이터셋
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08629160B2

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