Water → 8-Azido-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-4-amine

HRID 336141노트

반응식

HRID 336141 반응식
[N-:1]=[N+:2]=[N-:3].[Na+].CS(O[CH:10]1[CH2:18][CH2:17][C:16]2[N:12]([C:13]3[N:32]=[CH:31][N:30]=[C:29]([NH2:33])[C:14]=3[C:15]=2[C:19]2[CH:20]=[N:21][C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:11]1)(=O)=O.O>CN(C=O)C>[N:1]([CH:10]1[CH2:18][CH2:17][C:16]2[N:12]([C:13]3[N:32]=[CH:31][N:30]=[C:29]([NH2:33])[C:14]=3[C:15]=2[C:19]2[CH:20]=[N:21][C:22]3[C:27]([CH:28]=2)=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:11]1)=[N+:2]=[N-:3]

참가 물질

5

반응물 3

HCID 962WaterHCID 33557Sodium AzideHCID 867112814-Amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl methanesulfonate

생성물 1

HCID 867112828-Azido-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-4-amine수율 77%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

Sodium azide (361 mg) was added to a solution of 4-amino-5-(quinolin-3-yl)-6,7,8,9-tetrahydropyrimido[5,4-b]indolizin-8-yl methanesulfonate (758 mg) obtained in Step 9 in DMF (9 ml) at room temperature, and the mixture was stirred at 80° C. for 4 hours. After cooling, the reaction mixture was poured into water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain the title compound as a yellow solid (508 mg).

후처리

  1. temperatureAfter cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-21f0adb07a4a460ea9c3f56ae98b71de
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889666B2

반응 노트

불러오는 중…