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Ammonium formate → 2-[4-(1H-indol-3-ylmethyl)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide

HRID 914689
ノート
印刷プレビュー

反応式

HRID 914689 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]=[C:11]2[C:20]3[N:16]([C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18][N:19]=3)[C:15]3[CH:27]=[CH:28][CH:29]=[CH:30][C:14]=3[N:13]([CH2:31][C:32]([N:34]([CH:41]([CH3:43])[CH3:42])[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:33])[C:12]2=[O:44])=[CH:2]1.C([O-])=O.[NH4+]>[Pd].CCO>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH:11]2[C:20]3[N:16]([C:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[N:18][N:19]=3)[C:15]3[CH:27]=[CH:28][CH:29]=[CH:30][C:14]=3[N:13]([CH2:31][C:32]([N:34]([CH:41]([CH3:42])[CH3:43])[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:33])[C:12]2=[O:44])=[CH:2]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 1363524502-[4-(1H-indol-3-ylmethylene)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide

生成物 1

HCID 236606722-[4-(1H-indol-3-ylmethyl)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide収率 18.4%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒
HCID 702
Ethanol
溶媒
2 回

反応条件

温度
80 °C

実験手順

To 10% Pd/C and EtOH was added 2-[4-(1H-indol-3-ylmethylene)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide (0.71 g, 1.2 mmol). An additional 25 mL of EtOH was added followed by ammonium formate (0.77 g, 12.2 mmol). The reaction mixture was heated to 80° C. for 6 hours. The catalyst was removed by filtration through Celite® and the filtrate was concentrated. The residue was dissolved in ethyl acetate and the organic solution was washed with saturated NaHCO3. The organic phase was dried over sodium sulfate and concentrated. The crude product was purified by chromatography (0% to 18% acetone/methylene chloride) to give 128 mg of 2-[4-(1H-indol-3-ylmethyl)-5-oxo-1-phenyl-4,5-dihydro-2,3,6,10b-tetraaza-benzo[e]azulen-6-yl]-N-isopropyl-N-phenyl-acetamide as a racemic mixture. 1H NMR (CD2Cl2) δ 8.18 (s, 1H), 7.64 (dd, 2H), 7.55 (dd, 1H), 7.510-7.41 (m, 8H), 7.36 (dd, 1H), 7.25 (m, 3H), 7.09 (m, 2H), 7.027 (m, 1H), 6.85 (dd, 1H), 4.86 (m, 1H), 4.40 (br d, 1H), 4.04 (dd, 1H), 3.79 (m, 3H), 103 (dd, 6H); MS 581.4 (M+1).

後処理

  1. customThe catalyst was removed by filtration through Celite®
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe organic solution was washed with saturated NaHCO3
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated
  7. customThe crude product was purified by chromatography (0% to 18% acetone/methylene chloride)

出典と根拠

ORDレコード
ord-00cfc765d577435983b31111af8c1508
出典データセット
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07265104B2

反応ノート

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