Dichloromethane → HCID 131724535、化合物

HRID 1836571ノート

反応式

HRID 1836571 の反応式
O=[C:2]1[N:13]2[C:14]3[C:9]([CH2:10][CH2:11][CH2:12]2)=[CH:8][CH:7]=[CH:6][C:5]=3[CH:4]=[C:3]1[C:15](OCC)=O.CO[CH2:22][N:23](CC1C=CC=CC=1)C[Si](C)(C)C.FC(F)(F)C(O)=O.C(Cl)[Cl:44]>>[ClH:44].[ClH:44].[CH:6]1[CH:7]=[CH:8][C:9]2[CH2:10][CH2:11][CH2:12][N:13]3[C:14]=2[C:5]=1[C@@H:4]1[CH2:22][NH:23][CH2:15][C@@H:3]1[CH2:2]3

参加物

5

反応物 4

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 23498526Ethyl 2,3-dihydro-5-oxo-1H,5H-benzo[ij]quinolizine-6-carboxylate

生成物 1

HCID 131724535HCID 131724535、化合物収率 96%

反応条件

温度
40 °C

実験手順

To a solution of ethyl 5-oxo-2,3-dihydro-1H,5H-pyrido[3,2,1-ij]quinoline-6-carboxylate (25.0 g, 97 mmol) in 400 mL of methylene chloride was added N-(methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (46.1 g, 194 mmol) and trifluoroacetic acid (2.22 g, 19 mmol). The reaction mixture was stirred at 40° C. for 24 h. The reaction mixture was allowed to cool and was washed with sat'd aq. NaHCO3 and brine, dried (K2CO3) and concentrated in vacuo. The residue was purified by recrystallization from 4:1 hexane/ethyl acetate to afford 36.6 g (96%) of the title compound of Part B as an off white solid. 1H NMR (CDCl3) δ: 7.37-7.20 (m, 5H), 7.05-7.00 (m, 1H), 6.97-6.88 (m, 2H), 4.28-4.19 (m, 1H), 4.12-4.01 (m, 2H), 3.80-3.68 (m, 4H), 3.57 (ABq, 2H, JAB=10.2 Hz), 3.17 (app t, 1H, J=8.8 Hz), 2.85-2.77 (m, 2H), 2.49 (app t, 1H, J=9.5 Hz), 2.05-1.95 (m, 2H), 1.09 (t, 3H, J=7.0 Hz).

後処理

  1. temperatureto cool
  2. washwas washed with sat'd aq. NaHCO3 and brine
  3. dry with materialdried (K2CO3)
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by recrystallization from 4:1 hexane/ethyl acetate

出典と根拠

ORDレコード
ord-64ea401fa98947728836247a96c76b92
出典データセット
uspto-grants-2004_08
特許番号
US06777406B2

反応ノート

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