Dimethylformamide → 2-Chloro-N-{1-[2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide

HRID 1247501노트

반응식

HRID 1247501 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[C:8]([CH2:11][N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH:14]([NH:22][C:23]([C:25]2[NH:29][C:28]3[S:30][C:31]([Cl:33])=[CH:32][C:27]=3[CH:26]=2)=[O:24])[C:13]1=[O:34])(O)=[O:9].CCN=C=NCCCN(C)C.CN(C=O)C>CN(C)C1C=CN=CC=1.C1COCC1.O>[Cl:33][C:31]1[S:30][C:28]2[NH:29][C:25]([C:23]([NH:22][CH:14]3[CH2:15][C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[N:12]([CH2:11][C:8]([N:5]4[CH2:6][CH2:7][CH:2]([OH:1])[CH2:3][CH2:4]4)=[O:9])[C:13]3=[O:34])=[O:24])=[CH:26][C:27]=2[CH:32]=1

참가 물질

8

반응물 4

HCID 6228DimethylformamideHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 79341Piperidin-4-olHCID 10319016N-[1-(Carboxymethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide

생성물 1

HCID 100969462-Chloro-N-{1-[2-(4-hydroxypiperidin-1-yl)-2-oxoethyl]-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl}-6H-thieno[2,3-b]pyrrole-5-carboxamide수율 59%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

4-Dimethylaminopyridine (5 mg, 0.038 mmol) and 4-hydroxypiperidine (42 mg, 0.41 mmol) were added to a suspension of N-[1-(carboxymethyl)-2-oxo-1,2,3,4-tetrahydroquinolin-3-yl]-2-chloro-6H-thieno[2,3-b]pyrrole-5-carboxamide (Example 2; 150 mg, 0.38 mmol) and EDCI (79 mg, 0.41 mmol) in THF (0.5 mL) under an inert atmosphere. DMF (0.5 mL) was added and the mixture stirred at ambient temperature for 18 h. After pouring into water (10 mL) the resultant solid was filtered off and washed with 1M HCl aq. and water. Chromatography on silica gel (eluent gradient of CH2Cl2 to MeOH:CH2Cl2 (1:9)) afforded the title compound (109 mg, 59%) as an off white solid.

후처리

  1. filtrationwas filtered off
  2. washwashed with 1M HCl aq. and water

출처 및 근거

ORD 기록
ord-58b6a31d3a7e4952a59b5a823c0d804a
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07129249B2

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