4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-3-[cyclopropyl(hydroxy)methyl]-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide

HRID 1843058Notes

Reaction equation

HRID 1843058 reaction equation
[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[CH:19]1([CH:22]([OH:36])[C:23]2[C:27]([C:28]([F:31])([F:30])[F:29])=[C:26]([C:32]([OH:34])=O)[N:25]([CH3:35])[N:24]=2)[CH2:21][CH2:20]1.[NH2:37][C:38]1[CH:39]=[CH:40][C:41]([Cl:50])=[C:42]([CH:49]=1)[C:43]([NH:45][CH:46]1[CH2:48][CH2:47]1)=[O:44]>O1CCCC1>[Cl:50][C:41]1[CH:40]=[CH:39][C:38]([NH:37][C:32]([C:26]2[N:25]([CH3:35])[N:24]=[C:23]([CH:22]([CH:19]3[CH2:20][CH2:21]3)[OH:36])[C:27]=2[C:28]([F:29])([F:30])[F:31])=[O:34])=[CH:49][C:42]=1[C:43](=[O:44])[NH:45][CH:46]1[CH2:48][CH2:47]1

Participants

5

Reactant 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 167752405-amino-2-chloro-N-cyclopropylbenzamideHCID 585425253-[cyclopropyl(hydroxy)methyl]-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid

Product 1

HCID 67379064N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-3-[cyclopropyl(hydroxy)methyl]-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxamideYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

515 mg (1.86 mmol) of 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride are added to a solution of 410 mg (1.55 mmol) of 3-[cyclopropyl(hydroxy)methyl]-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxylic acid and 327 mg (1.55 mmol) of 5-amino-2-chloro-N-cyclopropylbenzamide in tetrahydrofuran (10 ml) and the mixture is stirred for six hours at room temperature. The reaction mixture is concentrated by evaporation, admixed with water, extracted with dichloromethane and the combined organic phases are dried over sodium sulphate. Following concentration by evaporation in vacuo, the solid is washed with dichloromethane to give 308 mg of (N-[4-chloro-3-(cyclopropylcarbamoyl)phenyl]-3-[cyclopropyl(hydroxy)methyl]-1-methyl-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (44%).

Workup

  1. concentrationThe reaction mixture is concentrated by evaporation
  2. extractionextracted with dichloromethane
  3. dry with materialthe combined organic phases are dried over sodium sulphate
  4. concentrationconcentration
  5. customby evaporation in vacuo
  6. washthe solid is washed with dichloromethane

Sources & evidence

ORD record
ord-b993c838a4a7425e9aed3528e5a442cb
Source dataset
uspto-grants-2015_02
Patent number
US08946234B2

Reaction notes

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