(Phenylethynyl)-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one → HCID 22266667、化合物

HRID 33304

反応式

HRID 33304 の反応式
C1(C#C[N:9]2[C:17]3[CH:16]=[CH:15][CH:14]=[C:13]4[C:18](=[O:22])[NH:19][CH2:20][CH2:21][C:11]([C:12]=34)=[CH:10]2)C=CC=CC=1>CO.[Pt]=O>[CH2:10]([C:10]1[NH:9][C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:18](=[O:22])[NH:19][CH2:20][CH2:21][C:11]=1[C:12]=23)[CH2:11][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

参加物

4

反応物 1

HCID 69274385(Phenylethynyl)-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one2 回

生成物 1

HCID 22266667HCID 22266667、化合物

試薬・触媒・溶媒 2

HCID 82844Platinum oxide (PtO)触媒HCID 887Methanol溶媒

反応条件

温度
24 °C

実験手順

2-Phenylethynyl-3,4,5,6-tetrahydro-1H-azepino[5,4,3-cd]indol-6-one (Compound 17) (37 mg, 0.13 mmol) and platinum oxide (1.5 mg, 0.05 mmol) were suspended in 2 mL MeOH under an argon atmosphere. The flask was flushed with hydrogen gas and the resulting mixture stirred at 24° C. under 1 atmosphere of hydrogen for 20 h. The catalyst was filtered off and the resulting solution concentrated, leaving a pale-yellow crystalline solid. Purification by radial chromatography (5% MeOH in CHCl3) followed by recrystallization (MeOH/CHCl3/hexanes) yielded 2-phenethyl-1,3,4,5-tetrahydro-azepino[5,4,3-cd]indol-6-one, 14 mg (37%), as a pale-yellow solid. mp 207-208° C.; 1H NMR (300 MHz, d6-DMSO) δ 2.60 (m, 2H), 2.95 (m, 4H), 3.26 (m, 2H), 7.17 (m, 6H), 7.46 (dd, 1H, J=7.8, 0.6 Hz), 7.61 (dd, 1H, J=7.5, 0.6 Hz), 7.90 (br t, 1H), 11.16 (br s, 1H); MS (FAB, MH+) 291; Anal. (C19H18N2O) C, H, N.

後処理

  1. customThe flask was flushed with hydrogen gas
  2. filtrationThe catalyst was filtered off
  3. concentrationthe resulting solution concentrated
  4. customleaving a pale-yellow crystalline solid
  5. customPurification by radial chromatography (5% MeOH in CHCl3)
  6. customfollowed by recrystallization (MeOH/CHCl3/hexanes)

出典と根拠

ORDレコード
ord-001bc565059c4788b663139ae4386a28
出典データセット
uspto-grants-2008_09
特許番号
US07429578B2

関連ノート

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