4-(1-methylpiperidin-4-yloxy)-2-phenylethynyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene → 4-(1-methylpiperidin-4-yloxy)-2-phenethyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

HRID 1773870노트

반응식

HRID 1773870 반응식
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([O:8][CH:9]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][N:14]3[C:10]2=[N:11][CH:12]=[C:13]3C#CC2C=CC=CC=2)[CH2:4][CH2:3]1>CO.O=[Pt]=O>[CH3:1][N:2]1[CH2:3][CH2:4][CH:5]([O:8][CH:9]2[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=3[CH2:16][CH2:15][N:14]3[C:10]2=[N:11][C:12]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13]3)[CH2:6][CH2:7]1

참가 물질

4

반응물 1

HCID 867039564-(1-methylpiperidin-4-yloxy)-2-phenylethynyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

생성물 1

HCID 867039574-(1-methylpiperidin-4-yloxy)-2-phenethyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 887Methanol용매

실험 절차

To a solution of 4-(1-methylpiperidin-4-yloxy)-2-phenylethynyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene (example 34) (50 mg, 0.126 mmole) in MeOH (1.3 mL) is added PtO2 (1.4 mg). The flask is evacuated and filled with hydrogen (balloon). The reaction mixture is stirred at room temperature overnight, then filtered on celite and cake washed with MeOH. Solvent is removed under reduced pressure. The residue is pre-purified by silica gel chromatography using (CH2Cl2:MeOH:NH4OH) as eluent with a gradient from (98:2:0.2) to (95:5:0.5) and the residue is submitted to a preparative thin-layer chromatography eluting with (CH2Cl2:MeOH:NH4OH) (9:1:1) to afford 4-(1-methylpiperidin-4-yloxy)-2-phenethyl-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene.

후처리

  1. customThe flask is evacuated
  2. additionfilled with hydrogen (balloon)
  3. filtrationfiltered on celite and cake
  4. washwashed with MeOH
  5. customSolvent is removed under reduced pressure
  6. customThe residue is pre-purified by silica gel chromatography
  7. washeluting with (CH2Cl2:MeOH:NH4OH) (9:1:1)

출처 및 근거

ORD 기록
ord-2b8cb98e5078401a91a8c9a60ed51827
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09255101B2

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