Cyclopentylamine → HCID 59253059, compound

HRID 884756Notes

Reaction equation

HRID 884756 reaction equation
[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[O:6][C:5]=1[NH:15][C@H:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:17][CH3:18])(=O)[CH3:2].[CH:25]1([NH2:30])[CH2:29][CH2:28][CH2:27][CH2:26]1>C(#N)C>[C:19]1([C@@H:16]([NH:15][C:5]([C:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:14])[N:30]([CH:25]3[CH2:29][CH2:28][CH2:27][CH2:26]3)[C:1]=2[CH3:2])=[O:6])[CH2:17][CH3:18])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 57733336HCID 57733336, compound

Product 1

HCID 59253059HCID 59253059, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 4-acetyl-3-((S)-1-phenyl-propylamino)-isochromen-1-one (60 mg) and cyclopentylamine (0.06 mL) in acetonitrile (0.2 mL) was heated under microwave irradiation at 170° C. for 15 min. The reaction mixture was partitioned between 2M HCl (3 mL) and ethyl acetate (3 mL). The organic phase was absorbed on SiO2 and flash chromatographed (20 g SiO2 column, gradient heptane-ethyl acetate, the product came out with 40% ethyl acetate) to give 18 mg of the title compound as a colourless solid. LC-MS (m/z) 389.5 (MH+); tR=1.52.

Workup

  1. customThe reaction mixture was partitioned between 2M HCl (3 mL) and ethyl acetate (3 mL)
  2. customThe organic phase was absorbed on SiO2 and flash
  3. customchromatographed (20 g SiO2 column, gradient heptane-ethyl acetate

Sources & evidence

ORD record
ord-edb10df5a2464706b27f7300be2f4003
Source dataset
uspto-grants-2012_08
Patent number
US08242134B2

Reaction notes

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