Triethylamine → 2-(Naphthalen-1-ylmethyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one

HRID 41542

반응식

HRID 41542 반응식
Cl.[C:2]1([N:12]2[CH:17](C)[CH2:16][CH2:15][C:14]3([CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[C:13]2=[O:24])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.Cl[C:26]1[CH:35]=[N:34][C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=1.[CH2:36](N(CC)CC)C>CCO>[C:11]1([CH2:2][N:12]2[CH2:17][CH2:16][CH2:15][C:14]3([CH2:19][CH2:20][N:21]([C:26]4[CH:35]=[N:34][C:33]5[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=5)[N:27]=4)[CH2:22][CH2:23]3)[C:13]2=[O:24])[C:6]2[C:7](=[CH:8][CH:3]=[CH:4][CH:5]=2)[CH:36]=[CH:9][CH:10]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 2389382-ChloroquinoxalineHCID 672523132-Naphthalen-1-yl-methyl-2,9-diaza-spiro[5.5]undecan-1-one hydrochloride

생성물 1

HCID 532591112-(Naphthalen-1-ylmethyl)-9-(quinoxalin-2-yl)-2,9-diazaspiro[5.5]undecan-1-one수율 68.7%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
160 °C

실험 절차

Crude 2-naphthalen-1-yl-methyl-2,9-diaza-spiro[5.5]undecan-1-one hydrochloride (100 mg, 0.29 mmol), 2-chloro-quinoxaline (81 mg, 0.49 mmol) and triethylamine (0.12 ml, 0.87 mmol) were dissolved in EtOH (1 ml) in a microwave tube. The tube was sealed and the suspension was heated at 160° C. over 20 min under microwave conditions. The solvent was removed under reduced pressure and the resulting crude product was purified by preparative reverse phase chromatography (Sun Fire C18 column, 16 min linear gradient: elution 20-60% (CH3CN in H2O (0.1% TFA)); flow rate 50 ml/min) to yield 87 mg (53%) of the title compound. [1H NMR (DMSO, 600 MHz) δ 8.86 (s, 1H), 8.07-8.00 (m, 1H), 7.98-7.91 (m, 1H), 7.86 (d, 1H, J=8.28 Hz), 7.82 (d, 1H, J=8.02 Hz), 7.64-7.56 (m, 2H), 7.56-7.50 (m, 2H), 7.48 (t, 1H), 7.38 (t, 1H), 7.34 (d, 1H, J=7.06 Hz), 4.98 (s, 2H), 4.37-4.26 (m, 2H), 3.46 (t, 2H), 3.23-3.10 (m, 2H), 2.20-2.08 (m, 2H), 1.93-1.82 (m, 2H), 1.80-1.70 (m, 2H), 1.67-1.53 (m, 2H), LCMS RtD=3.10 min, [M+H]+=437.2].

후처리

  1. customThe tube was sealed
  2. customThe solvent was removed under reduced pressure
  3. customthe resulting crude product was purified by preparative reverse phase chromatography (Sun Fire C18 column, 16 min linear gradient: elution 20-60% (CH3CN in H2O (0.1% TFA)); flow rate 50 ml/min)

출처 및 근거

ORD 기록
ord-4ae20f03f4a34420a6c9c32528453826
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08530648B2

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