Potassium Carbonate → HCID 178485586, compound

HRID 1842508Notes

Reaction equation

HRID 1842508 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:10](Cl)=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4].[NH:12]1[CH2:15][CH:14]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:18]=3[N:17]=2)[CH2:13]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[CH3:1][NH:2][C:3]([C:5]1[C:10]([N:12]2[CH2:15][CH:14]([C:16]3[NH:20][C:19]4[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:18]=4[N:17]=3)[CH2:13]2)=[N:9][CH:8]=[CH:7][N:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 596618233-chloro-N-methylpyrazine-2-carboxamideHCID 178477890HCID 178477890, compound

Product 1

HCID 178485586HCID 178485586, compoundYield 49.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-chloro-pyrazine-2-carboxylic acid methylamide (100 mg, 0.41 mmol) and 2-azetidin-3-yl-5-chloro-1H-benzoimidazole (as prepared by Preparation 5) (71 mg, 0.41 mmol) and K2CO3 (113 mg, 0.82 mmol) was dissolved in DMF (20 mL) and heated for 2 h at 100° C. The mixture was diluted with water (10 mL), and extracted with EtOAc (2×20 mL). The combined organic extracts were washed with water (5 mL) and brine (5 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by column chromatography to give the pure product (70 mg, yield 44%). [M+1] 343. IC50 (uM) 3.882.

Workup

  1. extractionextracted with EtOAc (2×20 mL)
  2. washThe combined organic extracts were washed with water (5 mL) and brine (5 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5363133e9f174f1fa10cb5f17f658bb2
Source dataset
uspto-grants-2015_02
Patent number
US08946230B2

Reaction notes

Loading…