Diisopropyl Ether → HCID 70392760, compound

HRID 246947Notes

Reaction equation

HRID 246947 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH2:8][CH2:7][NH:6][CH2:5]1.C(N(CC)CC)C.[F:16][C:17]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=1[NH:24][C:25]1[N:37]=[C:36](OS(C2C(C)=CC(C)=CC=2C)(=O)=O)[C:35]([F:51])=[CH:34][C:26]=1[CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(OC(C)C)(C)C>C(Cl)(Cl)Cl.O>[NH2:3][CH:4]1[CH2:8][CH2:7][N:6]([C:36]2[C:35]([F:51])=[CH:34][C:26]([CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:25]([NH:24][C:18]3[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:17]=3[F:16])[N:37]=2)[CH2:5]1

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 8471TriethylamineHCID 162125963-Aminopyrrolidine dihydrochlorideHCID 86741856HCID 86741856, compound

Product 1

HCID 70392760HCID 70392760, compoundYield 93.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

In 1.5 ml of chloroform was suspended 50 mg of 3-aminopyrrolidine dihydrochloride, and 110 mg of triethylamine was added thereto after which the resulting mixture was subjected to reaction at room temperature for 10 minutes. Thereafter, 150 mg of ethyl 2-[2-(2,4-difluorophenylamino)-5-fluoro-6-(2,4,6-trimethylbenzenesulfonyloxy)nicotinyl]acetate was added thereto, and the resulting mixture was subjected to reaction at room temperature for 1.5 hours. Subsequently, to the reaction mixture were added 5 ml of chloroform and 5 ml of water, and the organic layer was separated, washed successively with 5 ml of water and 5 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 2 ml of diisopropyl ether, after which crystals were collected by filtration to obtain 110 mg (yield 93.2%) of ethyl 2-[6-(3-amino-1-pyrrolidinyl)-2-(2,4-difluorophenylamino)-5-fluoronicotinyl]acetate. The physical properties of this compound were identical with those of the compound obtained in Example 29.

Workup

  1. additionwas added
  2. customafter which the resulting mixture was subjected to reaction at room temperature for 10 minutes
  3. customthe resulting mixture was subjected to reaction at room temperature for 1.5 hours
  4. customthe organic layer was separated
  5. washwashed successively with 5 ml of water and 5 ml of saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation under reduced pressure
  8. customto the crystalline material thus obtained
  9. filtrationafter which crystals were collected by filtration

Sources & evidence

ORD record
ord-26447a381d4b4ba0bc0a6d3562f642b9
Source dataset
uspto-grants-1987_11
Patent number
US04704459

Reaction notes

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