2-Chloro-N-pyridin-2-yl-acetamide → (R)-3-(2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(pyridin-2-ylamino)ethyl)-1-azoniabicyclo[2.2.2]octane chloride

HRID 469462

反応式

HRID 469462 の反応式
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)=[O:4].[S:12]1[CH:16]=[C:15]([CH:17]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:18]([O:20][C@@H:21]2[CH:26]3[CH2:27][CH2:28][N:23]([CH2:24][CH2:25]3)[CH2:22]2)=[O:19])[C:14]2[CH:36]=[CH:37][CH:38]=[CH:39][C:13]1=2>CCOC(C)=O>[Cl-:1].[S:12]1[CH:16]=[C:15]([CH:17]([NH:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:18]([O:20][C@@H:21]2[CH:26]3[CH2:27][CH2:28][N+:23]([CH2:2][C:3](=[O:4])[NH:5][C:6]4[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=4)([CH2:24][CH2:25]3)[CH2:22]2)=[O:19])[C:14]2[CH:36]=[CH:37][CH:38]=[CH:39][C:13]1=2

参加物

4

反応物 2

HCID 2894352-Chloro-N-pyridin-2-yl-acetamideHCID 58556957(R)-quinuclidin-3-yl 2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetate

生成物 1

HCID 54765168(R)-3-(2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(pyridin-2-ylamino)ethyl)-1-azoniabicyclo[2.2.2]octane chloride収率 22%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

2-Chloro-N-(pyridin-2-yl)acetamide (43.5 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 solvent was evaporated, and the residue was purified by preparative HPLC (Eluent: CH3CN, H2O). The product was triturated with i-Pr2O, filtered and dried under vacuum at room temperature to obtain (R)-3-(2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-(pyridin-2-ylamino)ethyl)-1-azoniabicyclo[2.2.2]octane chloride (31 mg, 21.6% yield).

後処理

  1. customThe solvent was evaporated
  2. customthe residue was purified by preparative HPLC (Eluent: CH3CN, H2O)
  3. customThe product was triturated with i-Pr2O
  4. filtrationfiltered
  5. customdried under vacuum at room temperature

出典と根拠

ORDレコード
ord-6ce602d1f2004402a1bb3b9b2b7a1f3d
出典データセット
uspto-grants-2014_01
特許番号
US08629160B2

関連ノート

読み込み中…