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

반응식

HRID 469462 반응식
[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

참가 물질

4

반응물 2

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

생성물 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 chloride수율 22%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6ce602d1f2004402a1bb3b9b2b7a1f3d
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629160B2

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