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Triethylamine → 7-(1-Acetylamino-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, ethyl ester

HRID 484212
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HRID 484212 반응식
[C:1]([NH:4][C:5]12[CH2:10][CH:9]1[CH2:8][NH:7][CH2:6]2)(=[O:3])[CH3:2].[CH2:11](N(CC)CC)[CH3:12].Cl[C:19]1[N:28]=[C:27]2[C:22]([C:23](=[O:40])[C:24]([C:37]([OH:39])=[O:38])=[CH:25][N:26]2[C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=2[F:36])=[CH:21][C:20]=1[F:41]>C(#N)C>[C:1]([NH:4][C:5]12[CH2:10][CH:9]1[CH2:8][N:7]([C:19]1[N:28]=[C:27]3[C:22]([C:23](=[O:40])[C:24]([C:37]([O:39][CH2:11][CH3:12])=[O:38])=[CH:25][N:26]3[C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:30]=3[F:36])=[CH:21][C:20]=1[F:41])[CH2:6]2)(=[O:3])[CH3:2]
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참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 105460847-Chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 157134351-Acetylamino-3-azabicyclo[3.1.0]hexane

생성물 1

HCID 157134587-(1-Acetylamino-3-azabicyclo[3.1.0]hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid, ethyl ester수율 100%

시약·촉매·용매 1

HCID 6342
Acetonitrile
용매

실험 절차

A mixture of 1-acetylamino-3-azabicyclo[3.1.0]hexane (60 mg, 0.28 mmol) and triethylamine (195 μl, 1.4 mmol) in acetonitrile (10 ml) was treated with the ethyl ester of 7-chloro-6-fluoro-1-(2,4-difluoro-phenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (95.6 mg, 0.25 mmol) and heated to 80° for 20 hours. The reaction mixture was concentrated in vacuo, diluted with chloroform and washed with saturated aqueous sodium bicarbonate. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was chromatographed on silica gel (eluant: 189:10:1 chloroform:methanol:conc. ammonium hydroxide) to yield the title product as a yellow oil (120.8 mg, 0.25 mmol, 100% yield). 1H NMR (CDCl3) 8.35 (s, 1H), 8.01 (d, J=13 Hz, 1H), 7.36 (m, 1H), 7.04 (m, 2H), 6.11 (bs, 1H), 4.35 (q, J=7 Hz, 2H), 3.96 (vbs, 1H), 3.69 (vbs, 3H), 1.96 (s, 3H), 1.73 (m, 1H), 1.37 (t, J=7 Hz, 3H), 1.06 (m, 1H), 0.71 (m, 1H).

후처리

  1. temperatureheated to 80° for 20 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. additiondiluted with chloroform
  4. washwashed with saturated aqueous sodium bicarbonate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was chromatographed on silica gel (eluant: 189:10:1 chloroform:methanol:conc. ammonium hydroxide)

출처 및 근거

ORD 기록
ord-2e2b5b85327f4d5d9eee26662335070c
출처 데이터셋
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05229396

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