[1-(5-Methyl-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)propyl]-carbamic acid benzyl ester → 2-(1-amino-propyl)-5-methyl-3-phenyl-3H-quinazolin-4-one

HRID 221303

반응식

HRID 221303 반응식
C(OC(=O)[NH:10][CH:11]([C:14]1[N:23]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:22](=[O:30])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[CH3:31])[N:15]=1)[CH2:12][CH3:13])C1C=CC=CC=1>C(O)C.[Pd]>[NH2:10][CH:11]([C:14]1[N:23]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:22](=[O:30])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[CH3:31])[N:15]=1)[CH2:12][CH3:13]

참가 물질

4

반응물 1

HCID 59841071[1-(5-Methyl-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)propyl]-carbamic acid benzyl ester

생성물 1

HCID 598410382-(1-amino-propyl)-5-methyl-3-phenyl-3H-quinazolin-4-one

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A catalytic amount of 10% Pd/C was added to a solution of compound 16 (691 mg, 1.62 mmol) in ethanol (8 mL). The resulting mixture was placed under a hydrogen atmosphere (balloon pressure) and allowed to stir at ambient temperature overnight. The reaction was filtered, and the filtrate concentrated in vacuo. The resulting crude residue was purified by flash chromatography to afford the free amine, compound 17, as a pale yellow oil. (ES): m/z 294 (M+H), 237. 1H NMR (300 MHz, DMSO-d6) δ 7.68 (t, 1H, J=7.7 Hz), 7.49-7.63 (m, 3H), 7.43-7.49 (m, 1H), 7.36-7.43 (m, 1H), 7.19-7.34 (m, 2H), 4.03-4.19 (m, 1H), 2.72 (s, 3H), 2.04 (br. s, 2H), 1.63-1.79 (m, 1H), 1.29-1.44 (m, 1H), 0.68 (t, 3H, J=7.3 Hz). The reaction described above and compound 17 are shown below.

후처리

  1. filtrationThe reaction was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customThe resulting crude residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-060ca4e2f4ac4d009b8c023ab7c25725
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08207153B2

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