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

HRID 232453
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 232453
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
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Komponenten

8

Edukt 4

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

Produkt 1

HCID 13821762Methyl 6-(3-amino-1-pyrrolidinyl)-2-(2,4-difluorophenylamino)-5-fluoronicotinateAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e5569e6b804447a08b36a57d3bc5c337
Quelldatensatz
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04851535

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