2-Bromo-1-(1,3-thiazol-2-yl)ethan-1-one → (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(2-oxo-2-(thiazol-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 469501노트

반응식

HRID 469501 반응식
[Br:1][CH2:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][N:9]=1)=[O:4].[CH3:10][O:11][C:12]1[N:17]=[CH:16][C:15]([CH:18]([NH:30][C:31]2[CH:32]=[C:33]([CH:39]=[CH:40][CH:41]=2)[C:34]([O:36][CH2:37][CH3:38])=[O:35])[C:19](=[O:29])[O:20][C@@H:21]2[CH:26]3[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]3)[CH2:22]2)=[CH:14][CH:13]=1>CCOC(C)=O>[Br-:1].[CH2:37]([O:36][C:34]([C:33]1[CH:32]=[C:31]([NH:30][CH:18]([C:15]2[CH:16]=[N:17][C:12]([O:11][CH3:10])=[CH:13][CH:14]=2)[C:19]([O:20][C@@H:21]2[CH:26]3[CH2:27][CH2:28][N+:23]([CH2:2][C:3](=[O:4])[C:5]4[S:6][CH:7]=[CH:8][N:9]=4)([CH2:24][CH2:25]3)[CH2:22]2)=[O:29])[CH:41]=[CH:40][CH:39]=1)=[O:35])[CH3:38]

참가 물질

4

반응물 2

HCID 27952122-Bromo-1-(1,3-thiazol-2-yl)ethan-1-oneHCID 58556990ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate

생성물 1

HCID 86660336(3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(2-oxo-2-(thiazol-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide수율 65.5%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

2-Bromo-1-(thiazol-2-yl)ethanone (23.4 mg, 0.11 mmol) was added to a solution of ethyl 3-(1-(6-methoxypyridin-3-yl)-2-oxo-2-((R)-quinuclidin-3-yloxy)ethylamino)benzoate (C65) (50 mg, 0.11 mmol) in EtOAc (2 ml). The reaction was stirred at room temperature overnight, and then the solvent was evaporated and the residue was triturated with Et2O, filtered and dried to obtain (3R)-3-(2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetoxy)-1-(2-oxo-2-(thiazol-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane bromide (46.5 mg, 63.3% yield).

후처리

  1. customthe solvent was evaporated
  2. customthe residue was triturated with Et2O
  3. filtrationfiltered
  4. customdried

출처 및 근거

ORD 기록
ord-5261f964604149e3a3e63212839d11d6
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629160B2

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