Diethyl Ether → Methyl 6-(3-acetylamino-1-pyrrolidinyl)-2-(2,4-difluorophenylamino)-5-fluoronicotinate

HRID 246932Notes

Reaction equation

HRID 246932 reaction equation
[NH2:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:16]([F:17])=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])[N:8]=2)[CH2:3]1.[C:27](OC(=O)C)(=[O:29])[CH3:28].C(OCC)C>C(Cl)(Cl)Cl>[C:27]([NH:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:16]([F:17])=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[C:9]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=3[F:26])[N:8]=2)[CH2:3]1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 13821762Methyl 6-(3-amino-1-pyrrolidinyl)-2-(2,4-difluorophenylamino)-5-fluoronicotinate

Product 1

HCID 13821764Methyl 6-(3-acetylamino-1-pyrrolidinyl)-2-(2,4-difluorophenylamino)-5-fluoronicotinateYield 99.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 6.5 ml of chloroform was dissolved 650 mg of methyl 6-(3-amino-1-pyrrolidinyl)-2-(2,4-difluorophenylamino)-5-fluoronicotinate, and 190 mg of acetic anhydride was added to the resulting solution, after which the resulting mixture was subjected to reaction at room temperature for 10 minutes. The solvent was then removed by distillation under reduced pressure. To the crystalline material thus obtained was added 2 ml of diethyl ether, after which crystals were collected by filtration to obtain 720 mg (yield 99.4%) of methyl 6-(3-acetylamino-1-pyrrolidinyl)-2-(2,4-difluorophenylamino)-5-fluoronicotinate having a melting point of 199°-200° C.

Workup

  1. additionwas added to the resulting solution
  2. customafter which the resulting mixture was subjected to reaction at room temperature for 10 minutes
  3. customThe solvent was then removed by distillation under reduced pressure
  4. customTo the crystalline material thus obtained
  5. filtrationafter which crystals were collected by filtration

Sources & evidence

ORD record
ord-8cd2aa378c1d410fb691eed74c8d5beb
Source dataset
uspto-grants-1987_11
Patent number
US04704459

Reaction notes

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