Potassium Carbonate → tert-Butyl 5-((1-((3-chloroquinolin-6-yl)methyl)-1H-pyrazole-4-carboxamido)methyl)-4,6-dimethylpyridin-2-ylcarbamate

HRID 928456Notes

Reaction equation

HRID 928456 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([NH:8][CH2:9][C:10]2[C:11]([CH3:25])=[CH:12][C:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[N:14][C:15]=2[CH3:16])=[O:7])[CH:3]=[N:2]1.CS(O[CH2:31][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[N:38]=[CH:37][C:36]([Cl:42])=[CH:35]2)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:42][C:36]1[CH:37]=[N:38][C:39]2[C:34]([CH:35]=1)=[CH:33][C:32]([CH2:31][N:1]1[CH:5]=[C:4]([C:6]([NH:8][CH2:9][C:10]3[C:11]([CH3:25])=[CH:12][C:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:22])[CH3:23])=[N:14][C:15]=3[CH3:16])=[O:7])[CH:3]=[N:2]1)=[CH:41][CH:40]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 58081315tert-Butyl 5-((1H-pyrazole-4-carboxamido)methyl)-4,6-dimethylpyridin-2-ylcarbamateHCID 86661853(3-Chloroquinolin-6-yl)methyl methanesulfonate

Product 1

HCID 58081248tert-Butyl 5-((1-((3-chloroquinolin-6-yl)methyl)-1H-pyrazole-4-carboxamido)methyl)-4,6-dimethylpyridin-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of tert-Butyl 5-((1H-pyrazole-4-carboxamido)methyl)-4,6-dimethylpyridin-2-ylcarbamate (145 mg, 0.421 mmol), (3-Chloroquinolin-6-yl)methyl methanesulfonate (143 mg, 0.421 mmol 80%) and K2CO3 (291 mg, 2.105 mmol) in Acetone (3 ml) was stirred for 20 h at 50° C. The reaction was quenched with H2O and extracted twice with DCM. The organic layer was dried with Na2SO4, filtered and evaporated to dryness to afford crude title compound. The crude product was purified by preparative HPLC (Macherey-Nagel Nucleosil 250×40 mm, 5 to 100% ACN and 0.1% TFA, flow 40 ml/min) to afford pure title compound. MS (Method V) [M+H]+=521.4.

Workup

  1. customThe reaction was quenched with H2O
  2. extractionextracted twice with DCM
  3. dry with materialThe organic layer was dried with Na2SO4
  4. filtrationfiltered
  5. customevaporated to dryness
  6. customto afford crude title compound
  7. customThe crude product was purified by preparative HPLC (Macherey-Nagel Nucleosil 250×40 mm, 5 to 100% ACN and 0.1% TFA, flow 40 ml/min)

Sources & evidence

ORD record
ord-90d97aef9ba24316b6d5cbd4671c6659
Source dataset
uspto-grants-2016_03
Patent number
US09290485B2

Reaction notes

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