Pyrrolidine → 5-(5-(Quinazolin-4-yloxy)pentyloxy)-2-((pyrrolidin-1-yl)methyl)-4H-pyran-4-one

HRID 2108868Notes

Reaction equation

CS(O[CH2:6][C:7]1[O:8][CH:9]=[C:10]([O:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[N:24]=[CH:23][N:22]=2)[C:11](=[O:13])[CH:12]=1)(=O)=O.[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1>ClCCl>[N:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:21]([O:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][O:14][C:10]2[C:11](=[O:13])[CH:12]=[C:7]([CH2:6][N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)[O:8][CH:9]=2)=[N:22][CH:23]=1

Participants

Conditions

Temperature: 45 °C

Procedure

Methanesulfonic acid 4-oxo-5-[5-(quinazolin-4-yloxy)-pentyloxy]-4H-pyran-2-ylmethyl ester 20 (100 mg, 0.23 mmol) was dissolved in dichloromethane (3 mL). Pyrrolidine (48 μL, 0.575 mmol) was added via syringe. The mixture was stirred at 45° C. for 1.5 h. .CH2Cl2 (75 ml) was added and the solution was washed with NaHCO3 10% (3×50 mL), brine (3×50 mL). The organic layer was dried over MgSO4, filtered and evaporated. The crude product was purified by column chromatography on silica using as eluent CH2Cl2:MeOH=90:10. 5-(5-(Quinazolin-4-yloxy)pentyloxy)-2-((pyrrolidin-1-yl)methyl)-4H-pyran-4-one EHT 5317 was obtained (30 mg, 35% yield) as a colourless oil.

Workup

washthe solution was washed with NaHCO3 10% (3×50 mL), brine (3×50 mL)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
customevaporated
customThe crude product was purified by column chromatography on silica using as eluent CH2Cl2

Sources & evidence

ORD record: ord-36d296f61eac49cebe1b2291f4a261c1
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514432B2

Reaction notes

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