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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 275206
ノート
印刷プレビュー

反応式

HRID 275206 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 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

生成物 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 ester収率 100%

試薬・触媒・溶媒 1

HCID 6342
Acetonitrile
溶媒

実験手順

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), 1H37 (t, J= 7 Hz, 3H), 1.06 (m, 1H), 0.71 (m, 1H).

後処理

  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)

出典と根拠

ORDレコード
ord-f5ce43b59e0e4736989a4038876e8c90
出典データセット
uspto-grants-1995_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05391763

反応ノート

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