Trifluoroacetic acid → 1-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine

HRID 2366708노트

반응식

HRID 2366708 반응식
[N:1]1([C:7](=[O:29])[CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[C:24]3[C:23]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[N:17]=[C:16]([NH2:25])[C:15]=3[N:14]=[C:13]2[CH2:26][CH2:27][CH3:28])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.FC(F)(F)C(O)=O>[Pt](=O)=O>[N:1]1([C:7](=[O:29])[CH2:8][CH2:9][CH2:10][CH2:11][N:12]2[C:24]3[C:23]4[CH2:22][CH2:21][CH2:20][CH2:19][C:18]=4[N:17]=[C:16]([NH2:25])[C:15]=3[N:14]=[C:13]2[CH2:26][CH2:27][CH3:28])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 574470661-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine

생성물 1

HCID 574470931-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine수율 28%

시약·촉매·용매 1

HCID 345198Adams' catalyst촉매

실험 절차

A mixture of 1-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-1H-imidazo[4,5-c]quinolin-4-amine (1.66 g, 4.19 mmol, prepared in Example 34), platinum (IV) oxide (1.5 g, 6.6 mmol), and trifluoroacetic acid (25 mL) was placed in a Parr vessel and shaken under hydrogen pressure (40 psi, 2.8×105 Pa) overnight. The reaction mixture was filtered through a layer of CELITE filter agent, and the filter cake was washed with ethanol. The filtrate was concentrated under reduced pressure, and the residue was purified by flash column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol). The resulting solid was triturated three times with 10% aqueous sodium hydroxide, isolated by filtration, and washed with water to provide 0.468 g of 1-(5-morpholin-4-yl-5-oxopentyl)-2-propyl-6,7,8,9-tetrahydro-1H-imidazo[4,5-c]quinolin-4-amine as a white solid, mp 158-160° C.

후처리

  1. filtrationThe reaction mixture was filtered through a layer of CELITE filter agent
  2. washthe filter cake was washed with ethanol
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was purified by flash column chromatography on silica gel (eluting with 95:5 dichloromethane:methanol)
  5. customThe resulting solid was triturated three times with 10% aqueous sodium hydroxide
  6. customisolated by filtration
  7. washwashed with water

출처 및 근거

ORD 기록
ord-cc223e39e1114ed3850fd03b3aecc87a
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697873B2

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