HCID 24701836, compound → HCID 178523377, compound

HRID 1843057Notes

Reaction equation

HRID 1843057 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:16])=[C:6]([CH:15]=1)[C:7]([NH:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[O:8].[F:17][C:18]([F:35])([C:23]1[C:27]([C:28]([F:31])([F:30])[F:29])=[C:26]([C:32](Cl)=[O:33])[NH:25][N:24]=1)[C:19]([F:22])([F:21])[F:20]>ClCCl.[Ag]C#N>[Cl:16][C:5]1[CH:4]=[CH:3][C:2]([NH:1][C:32]([C:26]2[NH:25][N:24]=[C:23]([C:18]([F:17])([F:35])[C:19]([F:20])([F:21])[F:22])[C:27]=2[C:28]([F:31])([F:29])[F:30])=[O:33])=[CH:15][C:6]=1[C:7](=[O:8])[NH:9][CH2:10][C:11]([F:12])([F:13])[F:14]

Participants

5

Reactant 2

HCID 24701836HCID 24701836, compoundHCID 178521131HCID 178521131, compound

Product 1

HCID 178523377HCID 178523377, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 178509332CID 101611454CatalystHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 212 mg (0.84 mmol) of 5-amino-2-chloro-N-(2,2,2-trifluoroethyl)benzamide and 168 mg (1.26 mmol) of silver(I) cyanide in 5.0 ml of dichloromethane is admixed with a solution of 265 mg (0.84 mmol) of 3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carbonyl chloride in 3.0 ml of dichloromethane and stirred for 16 h at room temperature. The suspension is then filtered over silica gel and the product is eluted with a mixture of dichloromethane and methanol (1:1). The solvents are removed under reduced pressure on a rotary evaporator and the resulting crude product is taken up in ethyl acetate. The organic phase is washed successively twice with 1M hydrochloric acid and once with saturated sodium chloride solution. The organic phase is then dried over magnesium sulphate, filtered and concentrated by evaporation under reduced pressure on a rotary evaporator. The crude product is then triturated with a mixture of dichloromethane, methyl tert-butyl ether and cyclohexane (1:1:1). The crude product obtained from the mother liquor is then purified by means of preparative HPLC. In this way, 49 mg of N-{4-chloro-3-[(2,2,2-trifluoroethyl)carbamoyl]phenyl}-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (11%) were obtained as a colourless solid.

Workup

  1. filtrationThe suspension is then filtered over silica gel
  2. washthe product is eluted with a mixture of dichloromethane and methanol (1:1)
  3. customThe solvents are removed under reduced pressure on a rotary evaporator
  4. washThe organic phase is washed successively twice with 1M hydrochloric acid and once with saturated sodium chloride solution
  5. dry with materialThe organic phase is then dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation under reduced pressure on a rotary evaporator
  8. customThe crude product is then triturated with a mixture of dichloromethane, methyl tert-butyl ether and cyclohexane (1:1:1)
  9. customThe crude product obtained from the mother liquor
  10. customis then purified by means of preparative HPLC

Sources & evidence

ORD record
ord-7003d45fe1ab4c929702106524d7edb2
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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