Triethylamine → 7-(1-tert-Butoxycarbonylamino-6-azaspiro[2.5]oct-6-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carbOxylic acid, ethyl ester

HRID 1654514ノート

反応式

HRID 1654514 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]1[C:11]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:18]1[N:27]=[C:26]2[C:21]([C:22](=[O:39])[C:23]([C:36]([OH:38])=[O:37])=[CH:24][N:25]2[C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=2[F:35])=[CH:20][C:19]=1[F:40].[CH2:41](N(CC)CC)[CH3:42].C(OCC)(=O)C.CCCCCC>C(#N)C.C(OCC)(=O)C.CCCCCC.CO>[C:1]([O:5][C:6]([NH:8][CH:9]1[C:11]2([CH2:12][CH2:13][N:14]([C:18]3[N:27]=[C:26]4[C:21]([C:22](=[O:39])[C:23]([C:36]([O:38][CH2:41][CH3:42])=[O:37])=[CH:24][N:25]4[C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=4[F:35])=[CH:20][C:19]=3[F:40])[CH2:15][CH2:16]2)[CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

7

反応物 4

HCID 8471TriethylamineHCID 105460847-Chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acidHCID 15282171tert-Butyl 6-azaspiro[2.5]octan-1-ylcarbamateHCID 21226206Ethyl acetate hexane

生成物 1

HCID 152821727-(1-tert-Butoxycarbonylamino-6-azaspiro[2.5]oct-6-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carbOxylic acid, ethyl ester収率 86%

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 21879739Ethyl acetate hexane methanol溶媒

実験手順

A solution of 1-tert-butoxycarbonylamino-6-azaspiro[2.5]octane (250 mg, 1.11 mmol), the ethyl ester of 7-chloro-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid (382 mg, 1.00 mmol) and triethylamine (0.78 ml, 5.55 mmol) in acetonitrile (15 ml) was heated at reflux overnight. Solvent was removed in vacuo and the residue was chromatographed on silica gel (eluents: 50% ethyl acetate/hexane, then 5:5:1 ethyl acetate/hexane/methanol) to afford the title product as an off-white solid (494 mg, 0.86 mmol, yield 86%).

後処理

  1. temperatureat reflux overnight
  2. customSolvent was removed in vacuo
  3. customthe residue was chromatographed on silica gel (eluents

出典と根拠

ORDレコード
ord-a71b47f913864fcda7384169f9095f30
出典データセット
uspto-grants-1995_04
特許番号
US05407943

反応ノート

読み込み中…