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Triethylamine → 7-(3,3-Dimethoxy-4-methylpyrrolidin-1-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,8-naphthyridine-3-carboxylic acid

HRID 846702
ノート
印刷プレビュー

反応式

HRID 846702 の反応式
[CH3:1][O:2][C:3]1([O:9][CH3:10])[CH:7]([CH3:8])[CH2:6][NH:5][CH2:4]1.C([O:13][C:14]([C:16]1[CH2:17][N:18]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=2[F:35])[C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([F:26])=[C:21](Cl)[N:20]=2)=[O:15])C.C(N(CC)CC)C>N1C=CC=CC=1>[CH3:1][O:2][C:3]1([O:9][CH3:10])[CH:7]([CH3:8])[CH2:6][N:5]([C:21]2[N:20]=[C:19]3[C:24]([CH:25]=[C:16]([C:14]([OH:15])=[O:13])[CH2:17][N:18]3[C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=3[F:35])=[CH:23][C:22]=2[F:26])[CH2:4]1
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 198833363,3-Dimethoxy-4-methylpyrrolidineHCID 867460661-(2,4-Difluorophenyl)-7-chloro-6-fluoro-1,8-naphthyridine-3-carboxylic acid ethyl ester

生成物 1

HCID 198832787-(3,3-Dimethoxy-4-methylpyrrolidin-1-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,8-naphthyridine-3-carboxylic acid収率 68.5%

試薬・触媒・溶媒 1

HCID 1049
Pyridine
溶媒

実験手順

In a reaction similar to that of Step 1, Example 387, into oven-dried glassware maintained under dry N2 were placed 0.132 g (0.91 mmol) of 3,3-dimethoxy-4-methylpyrrolidine (from Step 5 Example 183), 0.300 g (0.78 mmol) of 7-chloro-6-fluoro-1-(2,4-difluorophenyl)-1,8-naphthyridine-3-carboxylic acid ethyl ester, 12 mL of dry pyridine and 0.437 mL (3.1 mmol) of triethylamine. The reaction was stirred at room temperature for 15 hours, then the solvent was removed in a rotary evaporator. The residue was dissolved in methylene chloride and the product purified by column chromatography over silica gel, eluting with 0.5% increasing to 3% methanol/methylene chloride which was evaporated to afford 0.240 g of the title compound. This material was taken directly to the next step.

後処理

  1. customIn a reaction similar to that of Step 1, Example 387
  2. custominto oven-dried glassware
  3. temperaturemaintained under dry N2
  4. customthe solvent was removed in a rotary evaporator
  5. dissolutionThe residue was dissolved in methylene chloride
  6. customthe product purified by column chromatography over silica gel
  7. washeluting with 0.5%
  8. temperatureincreasing to 3% methanol/methylene chloride which
  9. customwas evaporated

出典と根拠

ORDレコード
ord-28e200da467b420dbfb0253a2b0b28c5
出典データセット
uspto-grants-1992_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05137892

反応ノート

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