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

HRID 1641444Notes

Reaction equation

HRID 1641444 reaction equation
[Br-:1].[NH4+].CC1C=CC(S(O[C:14]2[CH2:18][CH:17]([C:19](=[O:36])[NH:20][C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[C:28](=[O:35])[NH:29][CH:30]([CH:32]3[CH2:34][CH2:33]3)[CH3:31])[N:16]([C:37]3[C:42]([Cl:43])=[CH:41][CH:40]=[CH:39][N:38]=3)[N:15]=2)(=O)=O)=CC=1.CN(C)C=O>O>[Br:1][C:14]1[CH2:18][CH:17]([C:19]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[C:28](=[O:35])[NH:29][CH:30]([CH:32]2[CH2:34][CH2:33]2)[CH3:31])=[O:36])[N:16]([C:37]2[C:42]([Cl:43])=[CH:41][CH:40]=[CH:39][N:38]=2)[N:15]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 25514Ammonium BromideHCID 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 12.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
93 °C

Procedure

0.54 g of ammonium bromide 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 25 ml of N,N-dimethylformamide, followed by heating to 93° C. One hour later, the reaction liquid was poured to 50 ml of water, followed by extraction with diethyl ether. 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, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 1/1) to obtain 0.11 g of the desired product in the form of a paste.

Workup

  1. customOne hour later, the reaction liquid
  2. extractionfollowed by extraction with diethyl ether
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 1/1)

Sources & evidence

ORD record
ord-b4da1a5d97bc4c31bda340f25e109f2f
Source dataset
uspto-grants-2012_02
Patent number
US08115006B2

Reaction notes

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