Dimethylformamide dimethyl acetal → HCID 67172702, compound

HRID 470162Notes

Reaction equation

HRID 470162 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([C:21]([F:24])([F:23])[F:22])=[N:11][N:12]([C:15]3[N:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[C:13]=2[NH2:14])[CH:5]=[C:6]([Cl:8])[CH:7]=1.CO[CH:27](OC)[N:28]([CH3:30])[CH3:29]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([C:9]2[C:10]([C:21]([F:22])([F:24])[F:23])=[N:11][N:12]([C:15]3[N:20]=[CH:19][CH:18]=[CH:17][N:16]=3)[C:13]=2[N:14]=[CH:27][N:28]([CH3:30])[CH3:29])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 67173195HCID 67173195, compound

Product 1

HCID 67172702HCID 67172702, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.19 g (2.84 mmol) of 4-(3-bromo-5-chlorophenyl)-1-(pyrimidin-2-yl)-3-(trifluoromethyl)-1H-pyrazol-5-amine (known from WO 2008/077843 A) and 0.51 g (4.26 mmol) of dimethylformamide dimethyl acetal are dissolved in 20 ml of toluene and stirred under reflux for 18 hours. After cooling, the toluene solution is washed with water, the organic phase is separated off, dried with magnesium sulphate and filtered and the filtrate is concentrated under reduced pressure using a rotary evaporator. The residue is stirred with a solvent mixture of cyclohexane and ethyl acetate (vol. 1:1) and the precipiated solid is filtered off and air-dried. This gives 0.99 g (67% of theory) of the compound N′-[4-(3-bromo-5-chlorophenyl)-1-(pyrimidin-2-yl)-3-(trifluoromethyl)-1H-pyrazol-5-yl]-N,N-dimethylimidoformamide.

Workup

  1. temperatureunder reflux for 18 hours
  2. temperatureAfter cooling
  3. washthe toluene solution is washed with water
  4. customthe organic phase is separated off
  5. dry with materialdried with magnesium sulphate
  6. filtrationfiltered
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customa rotary evaporator
  9. stirringThe residue is stirred with a solvent mixture of cyclohexane and ethyl acetate (vol. 1:1)
  10. filtrationthe precipiated solid is filtered off
  11. customair-dried

Sources & evidence

ORD record
ord-efa3dd73dd154218b6f8d9a2d673c7bb
Source dataset
uspto-grants-2014_01
Patent number
US08629273B2

Reaction notes

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