Triethylamine → HCID 66686510, compound

HRID 1056458Notes

Reaction equation

HRID 1056458 reaction equation
[CH3:1][Si:2]([CH3:15])([CH3:14])[C:3]1[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=1[CH2:5][NH:6][CH:7]1[CH2:9][CH2:8]1.C(N(CC)CC)C.[F:23][C:24]1[N:28]([CH3:29])[N:27]=[C:26]([CH:30]([F:32])[F:31])[C:25]=1[C:33](Cl)=[O:34]>O1CCCC1>[CH:7]1([N:6]([CH2:5][C:4]2[CH:10]=[CH:11][CH:12]=[CH:13][C:3]=2[Si:2]([CH3:15])([CH3:14])[CH3:1])[C:33]([C:25]2[C:26]([CH:30]([F:32])[F:31])=[N:27][N:28]([CH3:29])[C:24]=2[F:23])=[O:34])[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 529205085-fluoro-1-methyl-3-difluoromethyl-1H-pyrazole-4-carbonyl chlorideHCID 66686853HCID 66686853, compound

Product 1

HCID 66686510HCID 66686510, compoundYield 66.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 175 mg (0.80 mmol) of N-[2-(trimethylsilyl)benzyl]cyclopropanamine in 5 ml of dry tetrahydrofurane was added 0.234 ml (1.68 mmol) of triethylamine, followed by a solution of 187 mg (0.88 mmol) of 5-fluoro-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carbonyl chloride in 3 ml of tetrahydrofurane. The reaction mixture was stirred under reflux for 3 hours. After cooling down, the reaction mixture was filtered, and the filtrate was evaporated under vacuum. The residue was dissolved in ethyl acetate/water. The aqueous phase was further extracted with ethyl acetate. The combined organic phase were dried and evaporated under vacuum to give 209 mg of the expected product.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling down
  3. filtrationthe reaction mixture was filtered
  4. customthe filtrate was evaporated under vacuum
  5. dissolutionThe residue was dissolved in ethyl acetate/water
  6. extractionThe aqueous phase was further extracted with ethyl acetate
  7. customThe combined organic phase were dried
  8. customevaporated under vacuum

Sources & evidence

ORD record
ord-d3f7e99c48c84710b969cabedfe5a55b
Source dataset
uspto-grants-2016_07
Patent number
US09398767B2

Reaction notes

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