Methanol → N-Methyl-4-[4-[2-(1-methyl-2-oxo-3,4-dihydroquinolin-5-yl)ethyl]piperazin-1-yl]benzofuran-2-carboxamide

HRID 1471668노트

반응식

HRID 1471668 반응식
[CH3:1][N:2]1[C:11]2[C:6](=[C:7]([CH2:12][CH:13]=O)[CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:15].[CH3:16][NH:17][C:18]([C:20]1[O:21][C:22]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[C:23]=2[CH:24]=1)=[O:19].CO.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.O>[CH3:16][NH:17][C:18]([C:20]1[O:21][C:22]2[CH:28]=[CH:27][CH:26]=[C:25]([N:29]3[CH2:34][CH2:33][N:32]([CH2:13][CH2:12][C:7]4[CH:8]=[CH:9][CH:10]=[C:11]5[C:6]=4[CH2:5][CH2:4][C:3](=[O:15])[N:2]5[CH3:1])[CH2:31][CH2:30]3)[C:23]=2[CH:24]=1)=[O:19]

참가 물질

7

반응물 4

HCID 887MethanolHCID 5049666Sodium triacetoxyborohydrideHCID 574059892-(1-Methyl-2-oxo-3,4-dihydroquinolin-5-yl)acetaldehydeHCID 57405990N-methyl-4-piperazin-1-yl-benzofuran-2-carboxamide

생성물 1

HCID 57388132N-Methyl-4-[4-[2-(1-methyl-2-oxo-3,4-dihydroquinolin-5-yl)ethyl]piperazin-1-yl]benzofuran-2-carboxamide

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

2-(1-Methyl-2-oxo-3,4-dihydroquinolin-5-yl)acetaldehyde (Example 1j, 0.50 g, 2.5 mmol) dissolved in dichloromethane (12 mL) was added to neat N-methyl-4-piperazin-1-yl-benzofuran-2-carboxamide (Example 1e, 0.542 g, 2.09 mmol). Methanol (2 mL) was added and the mixture was stirred at ambient temp for 20 min. Sodium triacetoxyborohydride (0.782 g, 3.69 mmol) was added and the mixture was stirred over the weekend. The mixture was diluted with dichloromethane and water. The organic phase was separated, dried over MgSO4, filtered, concentrated and purified by ISCO (0 to 8% 7 N ammonia/methanol in dichloromethane) to give of the title compound as a solid. Yield: 0.77 g, 70% 1H NMR (500 MHz, CDCl3) δ ppm 2.58-2.71 (m, 4H) 2.78 (br. s., 4H) 2.87-3.00 (m, 4H) 3.06 (d, 3H) 3.31 (br. s., 4H) 3.38 (s, 3H) 6.63 (d, 1H) 6.72 (d, 1H) 6.91 (d, 1H) 6.98 (d, 1H) 7.10 (d, 1H) 7.23 (t, 1H) 7.32 (t, 1H) 7.53 (s, 1H). MS m/z 447.2 [M+H]+.

후처리

  1. stirringthe mixture was stirred over the weekend
  2. customThe organic phase was separated
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by ISCO (0 to 8% 7 N ammonia/methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-42c01652dac14ebab6a907a4fb7487e9
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012457B2

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