2-(Chloroacetyl)thiophene → (3R)-3-(2-(benzo[b]thiophen-7-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride

HRID 469472노트

반응식

HRID 469472 반응식
[Cl:1][CH2:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)=[O:4].[S:10]1[CH:14]=[CH:13][C:12]2[CH:15]=[CH:16][CH:17]=[C:18]([CH:19]([NH:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:20]([O:22][C@@H:23]3[CH:28]4[CH2:29][CH2:30][N:25]([CH2:26][CH2:27]4)[CH2:24]3)=[O:21])[C:11]1=2.C(Cl)Cl.CO>C(#N)C>[Cl-:1].[S:10]1[CH:14]=[CH:13][C:12]2[CH:15]=[CH:16][CH:17]=[C:18]([CH:19]([NH:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:20]([O:22][C@@H:23]3[CH:28]4[CH2:27][CH2:26][N+:25]([CH2:2][C:3](=[O:4])[C:5]5[S:6][CH:7]=[CH:8][CH:9]=5)([CH2:30][CH2:29]4)[CH2:24]3)=[O:21])[C:11]1=2

참가 물질

5

반응물 3

HCID 27579252-(Chloroacetyl)thiopheneHCID 21226129Dichloromethane methanolHCID 58557003(R)-quinuclidin-3-yl 2-(benzo[b]thiophen-7-yl)-2-(phenylamino)acetate

생성물 1

HCID 86660328(3R)-3-(2-(benzo[b]thiophen-7-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride수율 16%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

2-Chloro-1-(thiophen-2-yl)ethanone (36.8 mg, 0.23 mmol) was added to a solution of (R)-quinuclidin-3-yl 2-(benzo[b]thiophen-7-yl)-2-(phenylamino)acetate (C27) (90 mg, 0.23 mmol) in acetonitrile (3 ml). The reaction was stirred at r.t. overnight. The solvent was removed under vacuum, and the crude product was triturated with Et2O. The compound was first purified by preparative HPLC (Eluent: CH3CN/H2O) and then by flash chromatography (DCM/MeOH=95/5) to obtain (3R)-3-(2-(benzo[b]thiophen-7-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(thiophen-2-yl)ethyl)-1-azoniabicyclo[2.2.2]octane chloride (20 mg, 16% yield).

후처리

  1. customThe solvent was removed under vacuum
  2. customthe crude product was triturated with Et2O
  3. customThe compound was first purified by preparative HPLC (Eluent: CH3CN/H2O)

출처 및 근거

ORD 기록
ord-a41e8da4dc46469092f98f14554f707a
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629160B2

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