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Chloroform → Methyl 6-(3-amino-1-pyrrolidinyl)-2-(2,4-difluorophenylamino)-5-fluoronicotinate

HRID 232453
ノート
印刷プレビュー

反応式

HRID 232453 の反応式
Cl[C:2]1[C:11]([F:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[F:21])[N:3]=1.Cl.Cl.[NH2:24][CH:25]1[CH2:29][CH2:28][NH:27][CH2:26]1.C(N(CC)CC)C.C(Cl)(Cl)Cl>CN(C)C=O.C(OCC)C.O>[NH2:24][CH:25]1[CH2:29][CH2:28][N:27]([C:2]2[C:11]([F:12])=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=3[F:21])[N:3]=2)[CH2:26]1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 13849310Methyl 6-chloro-2-(2,4-difluorophenylamino)-5-fluoronicotinateHCID 162125963-Aminopyrrolidine dihydrochloride

生成物 1

HCID 13821762Methyl 6-(3-amino-1-pyrrolidinyl)-2-(2,4-difluorophenylamino)-5-fluoronicotinate収率 95.1%

試薬・触媒・溶媒 3

HCID 962
Water
溶媒
HCID 3283Diethyl Ether溶媒
HCID 6228Dimethylformamide溶媒

実験手順

In 10 ml of N,N-dimethylformamide was suspended 1.00 g of methyl 6-chloro-2-(2,4-difluorophenylamino)-5-fluoronicotinate, and to the resulting suspension were added 750 mg of 3-aminopyrrolidine dihydrochloride, and 1.44 g of triethylamine, after which the resulting mixture was subjected to reaction at 70° C. for 30 minutes. Subsequently, to the reaction mixture were added 50 ml of chloroform and 50 ml of water, and the organic layer was separated, washed successively with 25 ml of water and 25 ml of saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and to the crystalline material thus obtained was added 5 ml of diethyl ether, after which crystals were collected by filtration to obtain 1.10 g (yield 95.1%) of methyl 6-(3-amino-1-pyrrolidinyl)-2-(2,4-difluorophenylamino)-5-fluoronicotinate having a melting point of 139°-140° C.

後処理

  1. customafter which the resulting mixture was subjected to reaction at 70° C. for 30 minutes
  2. customthe organic layer was separated
  3. washwashed successively with 25 ml of water and 25 ml of saturated aqueous sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure
  6. customto the crystalline material thus obtained
  7. filtrationafter which crystals were collected by filtration

出典と根拠

ORDレコード
ord-e5569e6b804447a08b36a57d3bc5c337
出典データセット
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04851535

反応ノート

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