HCID 22240025, compound → HCID 22240064, compound

HRID 892099Notes

Reaction equation

[CH:1]1([C:6]2[N:14]([CH2:15][O:16][CH3:17])[C:13]3[C:12]4=[N:18][CH:19]([CH2:21]OS(C)(=O)=O)[CH2:20][N:11]4[C:10](=[O:27])[N:9]([CH2:28][CH2:29][CH3:30])[C:8]=3[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[K].[C:32]1(=[O:42])[NH:36][C:35](=[O:37])[C:34]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:33]12>CN(C)C=O>[CH:1]1([C:6]2[N:14]([CH2:15][O:16][CH3:17])[C:13]3[C:12]4=[N:18][CH:19]([CH2:21][N:36]5[C:32](=[O:42])[C:33]6[C:34](=[CH:38][CH:39]=[CH:40][CH:41]=6)[C:35]5=[O:37])[CH2:20][N:11]4[C:10](=[O:27])[N:9]([CH2:28][CH2:29][CH3:30])[C:8]=3[N:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: 120 °C

Procedure

Compound 18 (500 mg, 0.98 mmol) obtained in Example 18 was dissolved in N,N-dimethylformamide (10 mL), to the solution was added phthalimide potassium salt (485 mg, 2.62 mmol, 2.7 equivalents), and the mixture was stirred at 120° C. for 4 hours. The reaction mixture was partitioned with ethyl acetate and water, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate and dried over anhydrous magnesium sulfate. After the reaction mixture was concentrated, the residue was crystallized from dichloromethane and diethyl ether to obtain the title compound (500 mg, 78%) as white crystals.

Workup

customThe reaction mixture was partitioned with ethyl acetate and water
washthe organic layer was washed with saturated aqueous sodium hydrogen carbonate
dry with materialdried over anhydrous magnesium sulfate
concentrationAfter the reaction mixture was concentrated
customthe residue was crystallized from dichloromethane and diethyl ether

Sources & evidence

ORD record: ord-35f54290f6184f1c921b3133084eb866
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07005430B2

Reaction notes

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