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Ammonium formate → (+/-)9-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-3-quinoxalin-2-yl nonanoic acid ethyl ester

HRID 860084
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인쇄 미리보기

반응식

HRID 860084 반응식
[CH2:1]([O:3][C:4](=[O:39])[CH2:5][CH:6]([C:29]1[CH:38]=[N:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:30]=1)[CH:7]=[CH:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)[N:14]=1)[CH3:2].C([O-])=O.[NH4+]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:39])[CH2:5][CH:6]([C:29]1[CH:38]=[N:37][C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[N:30]=1)[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=2)[N:14]=1)[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 2723923Ammonium formateHCID 69666596(+/-)9-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-3-quinoxalin-2-yl-non-4-enoic acid ethyl ester

생성물 1

HCID 69882476(+/-)9-[6-(4-Methoxy-benzylamino)-pyridin-2-yl]-3-quinoxalin-2-yl nonanoic acid ethyl ester수율 92.1%

시약·촉매·용매 2

HCID 23938Palladium촉매2회HCID 702
Ethanol
용매

실험 절차

A solution of the 22-4 (0.141 g, 0.268 mmol) in 25 mL absolute EtOH was treated with 10% Pd—C (0.015 g, 10% by wt) at room temperature under an argon atmosphere. Then ammonium formate (0.101 g, 1.61 mmol) was added and the heterogeneous mixture was refluxed for 30 minutes. The reaction was >50% complete (by ms). At this point, more Pd—C (0.008 g, 5% by wt) and NH4CO2 (0.050 g, 0.80 mmol) were added and the mixture refluxed for an additional 30. minutes (reaction complete by ms). The solution was then filtered through a Celite plug, washed with EtOH (75 mL), and concentrated in vacuo to afford 0.130 g 22-5.

후처리

  1. temperaturethe heterogeneous mixture was refluxed for 30 minutes
  2. temperaturethe mixture refluxed for an additional 30
  3. customminutes (reaction complete by ms)
  4. filtrationThe solution was then filtered through a Celite plug
  5. washwashed with EtOH (75 mL)
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c5cac8891a554236a78ee494bd2d725a
출처 데이터셋
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07153862B2

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