Potassium Carbonate → HCID 59401321, compound

HRID 2060894Notes

Reaction equation

HRID 2060894 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([CH2:12][NH2:13])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[OH:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH2:27])=[O:26])=[CH:23][CH:22]=1>CN(C=O)C>[NH2:13][CH2:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][CH:3]=[C:2]2[O:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([NH2:27])=[O:26])=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 650524-HydroxybenzamideHCID 59401376HCID 59401376, compound

Product 1

HCID 59401321HCID 59401321, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of C-(4-chloroquinolin-8-yl)methylamine (Preparation 89) (129 mg, 0.67 mmol), K2CO3 (186 mg, 1.34 mmol) and 4-hydroxybenzamide (110 mg, 0.81 mmol) in DMF (4 mL) were heated in a microwave at 100° C. for 40 min (150 W). Solvent removed in vacuo. The mixture was partitioned between EtOAc (50 mL) and water (20 mL), and the aqueous phase was further extracted with EtOAc (2×20 mL). The combined organic phase was washed with brine (20 mL) and dried (MgSO4). Solvent was removed in vacuo and the residue purified by column chromatography (0.25% to 0.75% NH4OH(aq), 2% to 8% MeOH in DCM) to give the title compound: RT=2.15 min; m/z (ES+)=294.1 [M+H]+.

Workup

  1. customSolvent removed in vacuo
  2. customThe mixture was partitioned between EtOAc (50 mL) and water (20 mL)
  3. extractionthe aqueous phase was further extracted with EtOAc (2×20 mL)
  4. washThe combined organic phase was washed with brine (20 mL)
  5. dry with materialdried (MgSO4)
  6. customSolvent was removed in vacuo
  7. customthe residue purified by column chromatography (0.25% to 0.75% NH4OH(aq), 2% to 8% MeOH in DCM)

Sources & evidence

ORD record
ord-a342471fe9354d15864dcab686197e36
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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