Dimethylformamide → (+/-)-3-(7-Methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-oxo-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-2-yl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

HRID 501968

반응식

HRID 501968 반응식
[OH:1][CH:2]([CH2:17][C:18]1[CH:26]=[C:25]([CH3:27])[C:24]2[C:20](=[CH:21][N:22]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:35])([CH3:34])[CH3:33])[N:23]=2)[CH:19]=1)[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH2:7][CH2:6]1)=[O:4].C(N(C(C)C)CC)(C)C.[NH:45]1[CH2:50][CH2:49][CH:48]([C:51]2[C:52](=[O:61])[NH:53][C:54]3[C:59]([CH:60]=2)=[CH:58][CH:57]=[CH:56][CH:55]=3)[CH2:47][CH2:46]1.O.ClCCl.CN(C)[CH:68]=[O:69]>ClCCl>[O:61]=[C:52]1[C:51]([CH:48]2[CH2:47][CH2:46][N:45]([C:68]([O:1][CH:2]([CH2:17][C:18]3[CH:26]=[C:25]([CH3:27])[C:24]4[C:20](=[CH:21][N:22]([CH2:28][O:29][CH2:30][CH2:31][Si:32]([CH3:33])([CH3:35])[CH3:34])[N:23]=4)[CH:19]=3)[C:3](=[O:4])[N:5]3[CH2:10][CH2:9][CH:8]([N:11]4[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]4)[CH2:7][CH2:6]3)=[O:69])[CH2:50][CH2:49]2)=[CH:60][C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[NH:53]1

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 81531Diisopropylethylamine2회HCID 183210463-(Piperidin-4-yl)quinolin-2(1H)-oneHCID 21908982Water methylene chlorideHCID 59424337(+/-)-2-hydroxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-1-one

생성물 1

HCID 59424342(+/-)-3-(7-Methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-oxo-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-2-yl 4-(2-oxo-1,2-dihydroquinolin-3-yl)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (±)-2-hydroxy-3-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)-1-(4-(piperidin-1-yl)piperidin-1-yl)propan-1-one (130 mg, 0.26 mmol) and diisopropylethylamine (91 μL, 0.52 mmol) in dichloromethane (1 mL) at 0° C. was added 4-nitrophenyl-chloroformate (57.6 mg, 1.10 equiv). The ice bath was removed and stirring continued for 4 h. The reaction was treated with a solution of 3-(piperidin-4-yl)quinolin-2(1H)-one (88.9 mg, 1.50 equiv) and diisopropylethylamine (91 μL, 0.52 mmol) in dimethylformamide (1 mL). The reaction was stirred at room temperature overnight. The reaction was poured into water/dichloromethane. The mixture was extracted with dichloromethane (2×) which was washed with saturated sodium bicarbonate, then water (2×), then brine, dried over magnesium sulfate, and concentrated. Column chromatography (5% to 20% methanol/dichloromethane) gave 112 mg (57%) as an oil.

후처리

  1. customThe ice bath was removed
  2. stirringThe reaction was stirred at room temperature overnight
  3. extractionThe mixture was extracted with dichloromethane (2×) which
  4. washwas washed with saturated sodium bicarbonate
  5. dry with materialwater (2×), then brine, dried over magnesium sulfate
  6. concentrationconcentrated
  7. customColumn chromatography (5% to 20% methanol/dichloromethane) gave 112 mg (57%) as an oil

출처 및 근거

ORD 기록
ord-816cd9f796b44fbc906ff79b46f1b9e6
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07772244B2

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