Potassium Carbonate → (+/-)-2-((2-Chloro-5-cyano-3-(2-(((4-methoxybenzyl)amino)methyl)morpholino)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

HRID 921916노트

반응식

HRID 921916 반응식
CS(O[CH2:6][CH:7]1[O:12][CH2:11][CH2:10][N:9]([C:13]2[CH:18]=[C:17]([C:19]#[N:20])[CH:16]=[C:15]([NH:21][C:22]3[N:27]=[C:26]([N:28]([CH:38]4[CH2:40][CH2:39]4)[CH2:29][C:30]4[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=4)[C:25]4=[N:41][CH:42]=[C:43]([C:44]#[N:45])[N:24]4[N:23]=3)[C:14]=2[Cl:46])[CH2:8]1)(=O)=O.[CH3:47][O:48][C:49]1[CH:56]=[CH:55][C:52]([CH2:53][NH2:54])=[CH:51][CH:50]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O.C(OCC)(=O)C>[Cl:46][C:14]1[C:13]([N:9]2[CH2:10][CH2:11][O:12][CH:7]([CH2:6][NH:54][CH2:53][C:52]3[CH:55]=[CH:56][C:49]([O:48][CH3:47])=[CH:50][CH:51]=3)[CH2:8]2)=[CH:18][C:17]([C:19]#[N:20])=[CH:16][C:15]=1[NH:21][C:22]1[N:27]=[C:26]([N:28]([CH:38]2[CH2:40][CH2:39]2)[CH2:29][C:30]2[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=2)[C:25]2=[N:41][CH:42]=[C:43]([C:44]#[N:45])[N:24]2[N:23]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 754524-MethoxybenzylamineHCID 89923151HCID 89923151, 화합물

생성물 1

HCID 89923206(+/-)-2-((2-Chloro-5-cyano-3-(2-(((4-methoxybenzyl)amino)methyl)morpholino)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile수율 64.9%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

A vial was charged with (+/−)-(4-(2-chloro-5-cyano-3-((7-cyano-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazin-2-yl)amino)phenyl)morpholin-2-yl)methyl methanesulfonate (56.5 mg, 0.085 mmol) and 4-methoxybenzylamine (33.3 μl, 0.255 mmol) in acetonitrile (904 μl). Potassium carbonate (58.7 mg, 0.425 mmol) was added and the vial was capped and heated at 80° C. ON. After cooling to room temperature, the reaction mixture was diluted with water and ethyl acetate. The aqueous layer was extracted with ethyl acetate (3×). The combined organics were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. (+/−)-2-((2-Chloro-5-cyano-3-(2-(((4-methoxybenzyl)amino)methyl)morpholino)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (38.9 mg) was isolated as a white solid and used as is in subsequent chemistry.

후처리

  1. customthe vial was capped
  2. temperatureAfter cooling to room temperature
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×)
  4. dry with materialThe combined organics were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-d61fa13ea78c4b6387f71cacabffbe03
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273057B2

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