[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 1625127

反応式

HRID 1625127 の反応式
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]

参加物

4

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

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), 1.29-1.4.4 (m, 1H), 0.68 (t, 3H, J=7.3 Hz). The reaction described above and compound 17 are shown below.

後処理

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

出典と根拠

ORDレコード
ord-dcae1f8373104b45a46e047f04cf8211
出典データセット
uspto-grants-2014_07
特許番号
US08779131B2

関連ノート

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