Hydrochloric Acid → HCID 13987858, compound

HRID 246939Notes

Reaction equation

HRID 246939 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[N:18]=[C:17]([O:19][S:20]([C:23]2[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=2[CH3:31])(=[O:22])=[O:21])[C:16]([F:32])=[CH:15][C:11]=1[C:12](Cl)=[O:13].[NH:33]1[CH:37]=[CH:36][N:35]=[CH:34]1.Cl.C(OC(C)C)(C)C>C(Cl)Cl.O.C(N(CC)CC)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:18]=[C:17]([O:19][S:20]([C:23]2[C:28]([CH3:29])=[CH:27][C:26]([CH3:30])=[CH:25][C:24]=2[CH3:31])(=[O:22])=[O:21])[C:16]([F:32])=[CH:15][C:11]=1[C:12]([N:33]1[CH:37]=[CH:36][N:35]=[CH:34]1)=[O:13]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 7914Diisopropyl EtherHCID 13987848HCID 13987848, compound

Product 1

HCID 13987858HCID 13987858, compoundYield 91.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

In 10 ml of methylene chloride was dissolved 500 mg of 2-(2,4-difluorophenylamino)-5-fluoro-6-(mesitylenesulfonyloxy)nicotinoyl chloride, and 1 ml of a methylene chloride solution containing 77 mg of imidazole and 120 mg of triethylamine was dropped into the resulting solution at -20° C., after which the resulting mixture was subjected to reaction at room temperature for 30 minutes. Subsequently, 5 ml of water was added to the reaction mixture, and the pH thereof was adjusted to 2.0 with 2N hydrochloric acid. 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 485 mg (yield 91.1%) of 1-[2-(2,4-difluorophenylamino)-5-fluoro-6-(mesitylenesulfonyloxy)nicotinoyl]imidazole having a melting point of 98°-101° C.

Workup

  1. additionwas dropped into the resulting solution at -20° C.
  2. customafter which the resulting mixture was subjected to reaction at room temperature for 30 minutes
  3. customThe organic layer was separated
  4. washwashed successively with 5 ml of water and 5 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. customto the crystalline material thus obtained
  8. filtrationafter which crystals were collected by filtration

Sources & evidence

ORD record
ord-c5b29405c33d4368805be6cfd1a39d3d
Source dataset
uspto-grants-1987_11
Patent number
US04704459

Reaction notes

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