Potassium Carbonate → HCID 178493186, 화합물

HRID 2271553노트

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HRID 2271553 반응식
CS(O[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([Br:24])[CH:22]=3)[N:17]=[CH:16][C:15]=2[C:25]([CH:27]2[CH2:29][CH2:28]2)=[O:26])[CH2:9][CH2:8]1)(=O)=O.Cl.[CH3:31][O:32][CH:33]1[CH2:37][CH2:36][NH:35][CH2:34]1.C([O-])([O-])=O.[K+].[K+].C(N(CC)C(C)C)(C)C>C(#N)C>[Br:24][C:21]1[CH:22]=[C:23]2[C:18](=[CH:19][CH:20]=1)[N:17]=[CH:16][C:15]([C:25]([CH:27]1[CH2:28][CH2:29]1)=[O:26])=[C:14]2[NH:13][C@H:10]1[CH2:9][CH2:8][C@H:7]([CH2:6][N:35]2[CH2:36][CH2:37][CH:33]([O:32][CH3:31])[CH2:34]2)[CH2:12][CH2:11]1

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 220176303-Methoxypyrrolidine hydrochlorideHCID 178505297HCID 178505297, 화합물

생성물 1

HCID 178493186HCID 178493186, 화합물수율 42.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

To a solution of (trans-4-((6-bromo-3-(cyclopropanecarbonyl)quinolin-4-yl)amino)cyclohexyl)methyl methanesulfonate (362 mg, 0.75 mmol) and 3-methoxypyrrolidine hydrochloride (410 mg, 2.98 mmol) in acetonitrile (15 mL) was added K2CO3 (1.24 g, 9 mmol) and KI (300 mg, 1.81 mmol) and N,N-diisopropylethylamine (0.5 mL, 2.9 mmol) and the reaction mixture was heated at 50° C. for 16 h and 80° C. for 24 h. The solution was cooled to room temperature, diluted with satd. aq. NaHCO3 and extracted with ethyl acetate. The combined organic layers were dried over anhydrous sodium sulfate, concentrated and purification by column chromatography (silica, 0-20% methanol/dichloromethane) to afford the desired product (155 mg, 42%) as an off-white solid. ESI MS m/z 486 [C25H32BrN3O2+H]+

후처리

  1. temperatureThe solution was cooled to room temperature
  2. additiondiluted with satd
  3. extractionaq. NaHCO3 and extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurification by column chromatography (silica, 0-20% methanol/dichloromethane)

출처 및 근거

ORD 기록
ord-41b5972ae61d42e0af5307975bd15ae3
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120749B2

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