Cyclohexanecarbonyl chloride → N-[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]-N-[2-phenyl-2-(tetrahydro-2H-pyran-4-yl)ethyl]cyclohexanecarboxamide

HRID 1943021노트

반응식

HRID 1943021 반응식
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH2:12][NH:13][CH2:14][CH:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:3]1=[O:28].CCN(C(C)C)C(C)C.[CH:38]1([C:44](Cl)=[O:45])[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>C(Cl)Cl>[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH2:12][N:13]([CH2:14][CH:15]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[C:44]([CH:38]2[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]2)=[O:45])[C:3]1=[O:28]

참가 물질

5

반응물 3

HCID 75938Cyclohexanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 584159371-methyl-3-({[2-phenyl-2-(tetrahydro-2H-pyran-4-yl)ethyl]amino}methyl)quinolin-2(1H)-one

생성물 1

HCID 58415921N-[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]-N-[2-phenyl-2-(tetrahydro-2H-pyran-4-yl)ethyl]cyclohexanecarboxamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To 1-methyl-3-({[2-phenyl-2-(tetrahydro-2H-pyran-4-yl)ethyl]amino}methyl)quinolin-2(1H)-one (46.5 mg, 0.124 mmol) in CH2Cl2 (3 ml) and added DIEA (0.043 ml, 0.247 mmol) then cyclohexanecarbonyl chloride (0.018 ml, 0.136 mmol). The reaction was stirred for 1 hour and then concentrated in vacuo. Purified by reversed-phase chromatography (15-75% ACN in water (with 0.5 ml/l NH4OH), 20×100 mm Phenomenex Gemini C18 column). Desired fractions were concentrated in vacuo. HRMS [M+H]1+ 487.2962. 400 MHz 1H NMR (CDCl3) δ 7.59-7.47 (m, 2 H), 7.37 (d, J=8.52 Hz, 1 H), 7.33-7.13 (m, 7 H), 4.26 (d, J=18.4, 1 H), 4.17-3.95 (m, 2 H), 3.88-3.76 (m, 2 H), 3.74 (s, 3 H), 3.44-3.23 (m, 3 H), 2.97-2.91 (m, 0.8 H, rotational isomer A), 2.67-2.62 (m, 0.2 H, rotational isomer B), 2.42-2.19 (m, 0.2 H, rotational isomer B), 2.15-2.08 (m, 0.8 H, rotational isomer A), 1.95-0.95 (m, 15 H). 29.4 mg, 49%.

후처리

  1. concentrationconcentrated in vacuo
  2. customPurified by reversed-phase chromatography (15-75% ACN in water (with 0.5 ml/l NH4OH), 20×100 mm Phenomenex Gemini C18 column)
  3. concentrationDesired fractions were concentrated in vacuo

출처 및 근거

ORD 기록
ord-dea2a79afd3c41978002274b5005ab5d
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389720B2

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