Dichloromethane → HCID 131724535, 화합물

HRID 1836571노트

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HRID 1836571 반응식
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

참가 물질

5

반응물 4

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

생성물 1

HCID 131724535HCID 131724535, 화합물수율 96%

반응 조건

온도
40 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-64ea401fa98947728836247a96c76b92
출처 데이터셋
uspto-grants-2004_08
특허 번호
US06777406B2

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