Ethyl Acetate → HCID 66807365, compound

HRID 1843885Notes

Reaction equation

HRID 1843885 reaction equation
[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[NH2:7][C:8]1[CH:17]=[C:16]2[C:11]([CH:12]=[CH:13][N:14]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][C:24]=3[CH3:25])[C:15]2=[O:18])=[CH:10][CH:9]=1.C(OC(=O)C)C>O>[CH3:25][C:24]1[CH:23]=[CH:22][N:21]=[CH:20][C:19]=1[N:14]1[CH:13]=[CH:12][C:11]2[C:16](=[CH:17][C:8]([NH:7][C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:5])=[CH:9][CH:10]=2)[C:15]1=[O:18]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 77637Cyclopropanecarbonyl chlorideHCID 66802210HCID 66802210, compound

Product 1

HCID 66807365HCID 66807365, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

TEA (25.1 mL, 0.1792 mmol) and cyclopropanecarbonyl chloride (12 mL, 0.1314 mmol) were added to a solution of 7-amino-2-(4-methyl-pyridin-3-yl)-2H-isoquinolin-1-one (I-24c: 30 mg, 0.1195 mmol) at 0° C. The resulting reaction mixture was stirred at 0° C. for 30 minutes. The reaction was monitored by TLC (100% ethylacetate). The reaction mixture was diluted with water and extracted with ethylacetate. The organic layer was washed with brine solution, dried over Na2SO4 and concentrated. Purification by column chromatography on silica gel (70% ethylacetate in hexane) afforded 10 mg of the product (26.2% yield).

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with ethylacetate
  3. washThe organic layer was washed with brine solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification by column chromatography on silica gel (70% ethylacetate in hexane)

Sources & evidence

ORD record
ord-344141d56d0744a784626239353d1c08
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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