Hydrogen chloride-ethyl acetate → HCID 178522298, compound

HRID 1624975Notes

Reaction equation

HRID 1624975 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:21]([NH:22][C:23](=[O:32])[C:24]3[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:31])=[CH:20][NH:19][N:18]=2)=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.Cl.CCOC(C)=O>CO.CCOC(C)=O>[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:21]([NH:22][C:23](=[O:32])[C:24]3[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=3[Cl:31])=[CH:20][NH:19][N:18]=2)=[O:16])[CH2:10][CH2:9]1

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 178452120HCID 178452120, compound

Product 1

HCID 178522298HCID 178522298, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-{[4-(2,6-dichloro-benzoylamino)-1H-pyrazole-3-carbonyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester (7.9 g) in MeOH (50 mL) and EtOAc (50 ml) was treated with sat. HCl-EtOAc (40 mL) then stirred at r.t. overnight. The product did not crystallise due to the presence of methanol, and therefore the reaction mixture was evaporated and the residue triturated with EtOAc. The resulting off white solid was collected by filtration, washed with EtOAc and sucked dry on the sinter to give 6.3 g of 4-(2,6-dichloro-benzoylamino)-1H-pyrazole-3-carboxylic acid piperidin-4-ylamide as the hydrochloride salt. (LC/MS: Rt 5.89, [M+H]+ 382/384).

Workup

  1. customThe product did not crystallise due to the presence of methanol
  2. customthe reaction mixture was evaporated
  3. customthe residue triturated with EtOAc
  4. filtrationThe resulting off white solid was collected by filtration
  5. washwashed with EtOAc
  6. customsucked dry on the sinter

Sources & evidence

ORD record
ord-037463f08d2241feb788791714c0a6db
Source dataset
uspto-grants-2014_07
Patent number
US08779147B2

Reaction notes

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