Potassium Carbonate → HCID 68414910, compound

HRID 659116Notes

Reaction equation

HRID 659116 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH2:12])[N:7]=1.CCN([CH:20]([CH3:22])[CH3:21])C(C)C.[C:23]([O-:26])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:3]([C:4]2[O:26][C:23]([C:21]3[CH:20]=[CH:22][CH:10]=[CH:9][CH:8]=3)=[CH:6][CH:5]=2)=[O:2])[N:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 54189349HCID 54189349, compound

Product 1

HCID 68414910HCID 68414910, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To acid (36) (100 mg, 0.53 mmol) was added thionyl chloride (0.5 mL), a catalytic amount of DMF (1 drop) and the reaction heated at 50° C. for 30 minutes. After cooling the solvent was concentrated in vacuo and azeotroped with toluene to provide the in situ acid chloride. To the acid chloride was added amine (38) (95 mg, 0.53 mmol) and DIPEA (69 mg, 0.53 mmol) in DCM (2 mL), and the reaction mixture stirred at ambient temperature overnight. K2CO3 (aq) was then added and the aqueous layer extracted with DCM. The organic layer was washed with water, dried (Na2SO4) and the solvent concentrated in vacuo. The residue was partially purified using column chromatography eluting with 50% EtOAc in heptane to give the title compound. Yield: 35 mg, 19%; LC-MS tr 1.67 min; HPLC Purity: 52%; MS (ES+) m/z 349 (M+H)

Workup

  1. extractionthe aqueous layer extracted with DCM
  2. washThe organic layer was washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationthe solvent concentrated in vacuo
  5. customThe residue was partially purified
  6. washeluting with 50% EtOAc in heptane

Sources & evidence

ORD record
ord-7680537e0768413285b1abbc14f0098d
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Reaction notes

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