Potassium Carbonate → HCID 86714221, compound

HRID 925509Notes

Reaction equation

HRID 925509 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[N:10]=2)[N:5]=[CH:4][C:3]=1[C:13]([O:15][CH2:16]C)=[O:14].[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([N:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]2)=[C:21]([C:38]([F:41])([F:40])[F:39])[CH:20]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.C(O)(C)(C)C>[C:34]([O:33][C:31]([N:28]1[CH2:27][CH2:26][N:25]([C:22]2[CH:23]=[CH:24][C:19]([NH:18][C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[N:10]=4)[N:5]=[CH:4][C:3]=3[C:13]([O:15][CH3:16])=[O:14])=[CH:20][C:21]=2[C:38]([F:40])([F:41])[F:39])[CH2:30][CH2:29]1)=[O:32])([CH3:37])([CH3:35])[CH3:36]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 14515789Ethyl 4,6-dichloro-1,5-naphthyridine-3-carboxylateHCID 18007750tert-Butyl 4-[4-amino-2-(trifluoromethyl)phenyl]piperazine-1-carboxylate

Product 1

HCID 86714221HCID 86714221, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6386tert-ButanolSolvent

Procedure

Ethyl 4,6-dichloro-1,5-naphthyridine-3-carboxylate (0.5 g, 1.84 mmol) and tert-butyl 4-(4-amino-2-(trifluoromethyl)phenyl)piperazine-1-carboxylate (0.766 g, 2.22 mmol) were dissolved in a mixture of dichloromethane (5 mL) and tert-butanol (5 mL), to the system added potassium carbonate (0.612 g, 4.43 mmol). The reaction mixture was stirred at room temperature for 24 h, suction filtrated, the solid was washed with 30 mL of dichloromethane, and the resulting wash solution and the filtrate were combined, concentrated under reduced pressure, and the resulting residue was recrystallized from diethyl ether to give 0.73 g of a pale yellow solid.

Workup

  1. filtrationsuction filtrated
  2. washthe solid was washed with 30 mL of dichloromethane
  3. washthe resulting wash solution
  4. concentrationconcentrated under reduced pressure
  5. customthe resulting residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-09d7ecc368c14b6ba40f69421dde11c4
Source dataset
uspto-grants-2016_03
Patent number
US09284315B2

Reaction notes

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