Dimethylamine → 1-[4-[3-chloro-4-(pyridin-2-ylmethoxy)-phenylamino]-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluoren-7-yl}-5-dimethylamino-pent-2-en-1-one

HRID 1887423노트

반응식

HRID 1887423 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:29]3[C:28]4[CH2:27][CH2:26][N:25]([C:30](=[O:40])[CH:31]=[CH:32][CH2:33][CH2:34]OS(C)(=O)=O)[CH2:24][C:23]=4[S:22][C:21]=3[N:20]=[CH:19][N:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:47][NH:48][CH3:49]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:29]3[C:28]4[CH2:27][CH2:26][N:25]([C:30](=[O:40])[CH:31]=[CH:32][CH2:33][CH2:34][N:48]([CH3:49])[CH3:47])[CH2:24][C:23]=4[S:22][C:21]=3[N:20]=[CH:19][N:18]=2)[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

참가 물질

5

반응물 3

HCID 674DimethylamineHCID 10796Cesium carbonateHCID 72332921methanesulfonic acid 5-{4-[3-chloro-4-(pyridine-2-ylmethoxy)-phenylamino]-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluoren-7-yl}-5-oxo-pent-3-enyl ester

생성물 1

HCID 668768191-[4-[3-chloro-4-(pyridin-2-ylmethoxy)-phenylamino]-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluoren-7-yl}-5-dimethylamino-pent-2-en-1-one수율 20%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

In a 25 ml rb flask were placed methanesulfonic acid 5-{4-[3-chloro-4-(pyridine-2-ylmethoxy)-phenylamino]-5,8-dihydro-6H-9-thia-1,3,7-triaza-fluoren-7-yl}-5-oxo-pent-3-enyl ester (0.15 g, 0.25 mmol) in DMF (5.0 ml) and to the solution was added cesium carbonate (0.16 g, 0.5 mmol) followed by dimethylamine (0.5 ml of 2M solution in THF) and heated at 50° C. overnight. The yellow solution was purified by HPLC twice to provide 27.5 mg of light brown solid (20.0%). 1H-NMR (DMSO-d6) δ 8.592-8.574 (m, 1H), 8.378 (s, 1H), 8.181 (s, 1H), 7.890-7.847 (m, 1H), 7.781-7.752 (m, 1H), 7.572-7.552 (d, 1H), 7.514-7.492 (m, 1H), 7.372-7.341 (m, 1H), 7.237-7.207 (m, 1H), 5.271 (s, 2H), 4.942-4.761 (m, 2H), 3.922-3.781 (m, 2H), 3.282-3.169 (m, 4H), 2.343 (m, 2H), 2.127-1.977 (m, 8H). MS m/e 549.1 (M+H), RT=2.26 min

후처리

  1. customIn a 25 ml rb flask were placed
  2. customThe yellow solution was purified by HPLC twice

출처 및 근거

ORD 기록
ord-77c8eda28a084b38b14f954214046784
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08501755B2

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