Pyridine → HCID 67372424, compound

HRID 1676894Notes

Reaction equation

HRID 1676894 reaction equation
[F:1][CH2:2][C:3]1[C:7]([C:8](Cl)=[O:9])=[CH:6][N:5]([CH3:11])[N:4]=1.[Cl:12][C:13]1[CH:14]=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[NH2:26])[CH:16]=[CH:17][C:18]=1[F:19].N1C=CC=CC=1.O1CCCC1>C1(C)C=CC=CC=1.C(OC)(C)(C)C>[Cl:12][C:13]1[CH:14]=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[NH:26][C:8]([C:7]2[C:3]([CH2:2][F:1])=[N:4][N:5]([CH3:11])[CH:6]=2)=[O:9])[CH:16]=[CH:17][C:18]=1[F:19]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8028TetrahydrofuranHCID 116009993'-chloro-4'-fluoro-2-aminobiphenylHCID 86621006HCID 86621006, compound

Product 1

HCID 67372424HCID 67372424, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

At room temperature, 0.27 g of 3-fluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride was added dropwise to a solution of 0.33 g of 3′-chloro-4′-fluoro-2-aminobiphenyl and 0.18 g of pyridine in 10 ml of toluene, and the mixture was stirred at room temperature for 16 hours. 10 ml of tetrahydrofuran and 30 ml of methyl tert-butyl ether were added, and the organic phase was washed successively with 2% strength hydrochloric acid, twice with 2% strength aqueous sodium hydroxide solution and then with dilute aqueous sodium chloride solution. The organic phase was dried and concentrated under reduced pressure. The crude product was triturated with 10 ml of diisopropyl ether and the solid that remained was filtered off with suction and dried. This gave 0.46 g of the desired product as a white powder of m.p. 133-134° C.

Workup

  1. washthe organic phase was washed successively with 2% strength hydrochloric acid, twice with 2% strength aqueous sodium hydroxide solution
  2. customThe organic phase was dried
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was triturated with 10 ml of diisopropyl ether
  5. filtrationthe solid that remained was filtered off with suction
  6. customdried

Sources & evidence

ORD record
ord-4e7ab908b9d84c2197b675797d1e623e
Source dataset
uspto-grants-2011_08
Patent number
US08008232B2

Reaction notes

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