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 469472ノート

反応式

HRID 469472 の反応式
[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

参加物

5

反応物 3

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

生成物 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 chloride収率 16%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-a41e8da4dc46469092f98f14554f707a
出典データセット
uspto-grants-2014_01
特許番号
US08629160B2

反応ノート

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