3-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chloride → Sedaxane

HRID 1803097Notes

Reaction equation

HRID 1803097 reaction equation
[F:1][CH:2]([F:12])[C:3]1[C:7]([C:8](Cl)=[O:9])=[CH:6][N:5]([CH3:11])[N:4]=1.[CH:13]1([CH:23]2[CH2:25][CH2:24]2)[CH2:15][CH:14]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH2:22]>C1(C)C=CC=CC=1>[CH:13]1([CH:23]2[CH2:25][CH2:24]2)[CH2:15][CH:14]1[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:8]([C:7]1[C:3]([CH:2]([F:12])[F:1])=[N:4][N:5]([CH3:11])[CH:6]=1)=[O:9]

Participants

4

Reactant 2

HCID 153401103-(Difluoromethyl)-1-methyl-1 H-pyrazole-4-carbonyl chlorideHCID 167270602-Bicyclopropyl-2-yl-phenylamine

Product 1

HCID 11688533Sedaxane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
85 °C

Procedure

16.7 g (0.086 mol, 98% pure) of 3-difluoromethyl-1-methyl-1H-pyrazole-4-carbonyl chloride were dissolved at 25° C. in 48.0 g of toluene. The solution was evacuated to 400 mbar and heated to 85° C. Subsequently, within 45 min, 15.0 g (0.087 mol) of 2-bicyclopropyl-2-ylphenylamine, dissolved in 51.6 g of toluene, were metered in and the reaction mixture was stirred for another 1 h. After venting and cooling to 25° C., the mixture was stirred overnight. Subsequently, the mixture was concentrated under reduced pressure and dried. The yield was 27.3 g (96%).

Workup

  1. customThe solution was evacuated to 400 mbar
  2. temperaturecooling to 25° C.
  3. stirringthe mixture was stirred overnight
  4. concentrationSubsequently, the mixture was concentrated under reduced pressure
  5. customdried

Sources & evidence

ORD record
ord-4669792b2001480695e037605dd3dcaa
Source dataset
uspto-grants-2013_01
Patent number
US08350046B2

Reaction notes

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