Trifluoroacetic acid → 4-(Benzyloxy)-1-(10-methyl-1,2,3,4,5,10-hexahydroazepino[3,4-b]indol-8-yl)pyridin-2(1H)-one

HRID 474899ノート

反応式

HRID 474899 の反応式
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:28][CH2:27][CH2:26][C:25]2[C:24]3[C:19](=[CH:20][C:21]([N:29]4[CH:34]=[CH:33][C:32]([O:35][CH2:36][C:37]5[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=5)=[CH:31][C:30]4=[O:43])=[CH:22][CH:23]=3)[N:18]([CH3:44])[C:17]=2[CH2:16]1)=O)(C)(C)C>C(Cl)Cl>[CH2:36]([O:35][C:32]1[CH:33]=[CH:34][N:29]([C:21]2[CH:20]=[C:19]3[C:24]([C:25]4[CH2:26][CH2:27][CH2:28][NH:15][CH2:16][C:17]=4[N:18]3[CH3:44])=[CH:23][CH:22]=2)[C:30](=[O:43])[CH:31]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 58093460tert-Butyl-8-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-10-methyl-3,4,5,10-tetrahydroazepino[3,4-b]indole-2(1H)-carboxylate

生成物 1

HCID 498694884-(Benzyloxy)-1-(10-methyl-1,2,3,4,5,10-hexahydroazepino[3,4-b]indol-8-yl)pyridin-2(1H)-one収率 73%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Trifluoroacetic acid (1.0 mL) was added to a solution of tert-butyl-8-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-10-methyl-3,4,5,10-tetrahydroazepino[3,4-b]indole-2(1H)-carboxylate (54 mg, 0.11 mmol) in CH2Cl2 (2.0 mL), and the resulting solution was stirred at ambient temperature for 30 min. The mixture was carefully quenched with saturated NaHCO3 solution until the solution was basic. The mixture was extracted with CH2Cl2 (3×25 mL). The combined organic extracts were washed with brine (50 mL), dried over Na2SO4 and concentrated to dryness under reduced pressure. Flash chromatography (12 g ISCO column, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 5 column volumes, increased to 0:100 over 20 column volumes and held for 15 column volumes) provided the title compound (31 mg, 73%) as an off-white solid: 1H NMR (500 MHz, CDCl3) δ 7.53 (d, J=8.5 Hz, 1H), 7.43-7.36 (m, 5H), 7.30 (d, J=7.5 Hz, 1H), 7.23 (d, J=2.0 Hz, 1H), 6.99 (dd, J=8.0, 1.5 Hz, 1H), 6.08 (d, J=2.5 Hz, 1H), 6.03 (dd, J=7.5, 3.0 Hz, 1H), 5.05 (s, 2H), 4.10 (s, 2H), 3.64 (s, 3H), 3.23 (t, J=5.5 Hz, 2H), 2.92 (t, J=6.0 Hz, 2H), 1.90-1.86 (s, 2H); ESI MS m/z 400 [M+H]+.

後処理

  1. customThe mixture was carefully quenched with saturated NaHCO3 solution until the solution
  2. extractionThe mixture was extracted with CH2Cl2 (3×25 mL)
  3. washThe combined organic extracts were washed with brine (50 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to dryness under reduced pressure
  6. temperatureFlash chromatography (12 g ISCO column, CH2Cl2/(80:18:2 CH2Cl2/MeOH/NH4OH), 100:0 for 5 column volumes, increased to 0:100 over 20 column volumes and held for 15 column volumes)

出典と根拠

ORDレコード
ord-c5c8ebd3f301446caac0b0716d8ada00
出典データセット
uspto-grants-2014_01
特許番号
US08637501B2

反応ノート

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