Diisopropylethylamine → (S)-N-ethyl-4-(4-((6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido[1,2-a:3',2'-e]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide

HRID 69632노트

반응식

HRID 69632 반응식
O[CH2:2][C:3]1[CH:12]=[N:11][C:10]2[N:9]3[CH2:13][CH2:14][CH2:15][CH2:16][C@H:8]3[C:7](=[O:17])[NH:6][C:5]=2[CH:4]=1.[I-].C(C[P+](C)(C)C)#N.CCN(C(C)C)C(C)C.[CH2:35]([NH:37][C:38](=[O:51])[C:39]1[CH:44]=[CH:43][C:42]([N:45]2[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]2)=[CH:41][CH:40]=1)[CH3:36]>>[CH2:35]([NH:37][C:38](=[O:51])[C:39]1[CH:40]=[CH:41][C:42]([N:45]2[CH2:46][CH2:47][N:48]([CH2:2][C:3]3[CH:12]=[N:11][C:10]4[N:9]5[CH2:13][CH2:14][CH2:15][CH2:16][C@H:8]5[C:7](=[O:17])[NH:6][C:5]=4[CH:4]=3)[CH2:49][CH2:50]2)=[CH:43][CH:44]=1)[CH3:36]

참가 물질

5

반응물 4

HCID 81531DiisopropylethylamineHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 28749590N-ethyl-4-(piperazin-1-yl)benzamideHCID 58324368(S)-3-(hydroxymethyl)-7,8,9,10-tetrahydro-5H-dipyrido[1,2-a:3',2'-e]pyrazin-6(6aH)-one

생성물 1

HCID 58324394(S)-N-ethyl-4-(4-((6-oxo-6,6a,7,8,9,10-hexahydro-5H-dipyrido[1,2-a:3',2'-e]pyrazin-3-yl)methyl)piperazin-1-yl)benzamide

반응 조건

온도
90 °C

실험 절차

To a suspension of (S)-3-(hydroxymethyl)-7,8,9,10-tetrahydro-5H-dipyrido[1,2-a:3′,2′-e]pyrazin-6(6aH)-one (800 mg, 3.43 mmol) was added (cyanomethyl)trimethylphosphonium iodide (1000 mg, 4.12 mmol) and DIEA (1797 μl, 10.29 mmol) and N-ethyl-4-(piperazin-1-yl)benzamide (800 mg, 3.43 mmol)). The vial was heated to 90° C. for 16 hours. The crude reaction was cooled to RT and filtered. The resulting solid were collected and suspended in EtOH (24 mL), heated to reflux, then cooled to RT and filtered. The resulting material was rinsed with EtOH to give a white solid.

후처리

  1. customThe crude reaction
  2. temperaturewas cooled to RT
  3. filtrationfiltered
  4. customThe resulting solid were collected
  5. temperatureheated
  6. temperatureto reflux
  7. temperaturecooled to RT
  8. filtrationfiltered
  9. washThe resulting material was rinsed with EtOH
  10. customto give a white solid

출처 및 근거

ORD 기록
ord-880cab0cc15044c6b8837ec2e06e8aa2
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822470B2

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