Hydrochloric Acid → Ethyl 2-[2-(2,4-difluorophenylamino)-6-ethylthio-5-fluoronicotinoyl]acetate

HRID 232465ノート

反応式

HRID 232465 の反応式
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:23]=[C:22](OS(C2C(C)=CC(C)=CC=2C)(=O)=O)[C:21]([F:37])=[CH:20][C:11]=1[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:13].[CH2:38]([SH:40])[CH3:39].C(N(CC)CC)C.Cl>CN(C)C=O.O.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:23]=[C:22]([S:40][CH2:38][CH3:39])[C:21]([F:37])=[CH:20][C:11]=1[C:12]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:13]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 8471TriethylamineHCID 13849317Ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-(2,4,6-trimethylbenzenesulfonyloxy)nicotinoyl]acetate

生成物 1

HCID 13849319Ethyl 2-[2-(2,4-difluorophenylamino)-6-ethylthio-5-fluoronicotinoyl]acetate収率 67.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

In 1 ml of N,N-dimethylformamide was dissolved 100 mg of ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-(2,4,6-trimethylbenzenesulfonyloxy)nicotinoyl]acetate, and 17 mg of ethanethiol and 28 mg of triethylamine were added thereto, after which the resulting mixture was subjected to reaction at room temperature for 4 hours. Subsequently, to the reaction mixture were added 3 ml of ethyl acetate and 3 ml of water, and the pH thereof was adjusted to 1.0 with 2N hydrochloric acid. The organic layer was separated, washed successively with 2 ml of water and 2 ml of saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: benzene-n-hexane (1:2 by volume)] to obtain 50 mg (yield 67.4%) of ethyl 2-[2-(2,4-difluorophenylamino)-6-ethylthio-5-fluoronicotinoyl]acetate. The physical properties of this compound were identical with those of the compound obtained in Example 19.

後処理

  1. additionwere added
  2. customafter which the resulting mixture was subjected to reaction at room temperature for 4 hours
  3. customThe organic layer was separated
  4. washwashed successively with 2 ml of water and 2 ml of saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure
  7. customthe residue thus obtained
  8. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: benzene-n-hexane (1:2 by volume)]

出典と根拠

ORDレコード
ord-8f6911ed7ed647cc96a58b18620dc400
出典データセット
uspto-grants-1989_07
特許番号
US04851535

反応ノート

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