Toluene → 3-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazole-5-carboxamide

HRID 1641446Notes

Reaction equation

HRID 1641446 reaction equation
O.O.[Br-:3].[Ca+2].[Br-].CC1C=CC(S(O[C:17]2[CH2:21][CH:20]([C:22](=[O:39])[NH:23][C:24]3[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=3[C:31](=[O:38])[NH:32][CH:33]([CH:35]3[CH2:37][CH2:36]3)[CH3:34])[N:19]([C:40]3[C:45]([Cl:46])=[CH:44][CH:43]=[CH:42][N:41]=3)[N:18]=2)(=O)=O)=CC=1.C1(C)C=CC=CC=1.C(=O)([O-])O.[Na+]>O>[Br:3][C:17]1[CH2:21][CH:20]([C:22]([NH:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[C:31](=[O:38])[NH:32][CH:33]([CH:35]2[CH2:37][CH2:36]2)[CH3:34])=[O:39])[N:19]([C:40]2[C:45]([Cl:46])=[CH:44][CH:43]=[CH:42][N:41]=2)[N:18]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 516892Sodium BicarbonateHCID 21694667Calcium;dibromide;dihydrateHCID 866399065-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenylcarbamoyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl 4-methylbenzenesulfonate

Product 1

HCID 441856063-bromo-N-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazole-5-carboxamideYield 172.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

0.25 g of calcium bromide dihydrate was added to a mixed liquid comprising 1.0 g of 5-(4-chloro-2-(1-cyclopropylethylcarbamoyl)phenylcarbamoyl)-1-(3-chloropyridin-2-yl)-4,5-dihydro-1H-pyrazol-3-yl 4-methylbenzenesulfonate and 10 ml of toluene, followed by heating at about 90° C. for 6.5 hours. After the reaction liquid was stood to cool, 0.41 g of sodium hydrogen carbonate and 10 ml of water were added to the reaction liquid, followed by stirring. After liquid-liquid separation, the organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 0.96 g of the crude desired product.

Workup

  1. customAfter the reaction liquid
  2. temperatureto cool
  3. customAfter liquid-liquid separation
  4. washthe organic layer was washed with a saturated sodium chloride aqueous solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-66d8a1cae51e4f03add0c2a1f15b3f3d
Source dataset
uspto-grants-2012_02
Patent number
US08115006B2

Reaction notes

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