1-Methylpiperazine → 5-(5-(7-(Trifluoromethyl)quinolin-4-yloxy)pentyloxy)-2-((4-methylpiperazin-1-yl)methyl)-4H-pyran-4-one

HRID 2108863Notes

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][C:27]([C:31]([F:34])([F:33])[F:32])=[CH:28][CH:29]=3)[N:24]=[CH:23][CH:22]=2)[C:11](=[O:13])[CH:12]=1)(=O)=O.[CH3:35][N:36]1[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]1>ClCCl>[F:34][C:31]([F:33])([F:32])[C:27]1[CH:26]=[C:25]2[C:30]([C:21]([O:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][O:14][C:10]3[C:11](=[O:13])[CH:12]=[C:7]([CH2:6][N:39]4[CH2:40][CH2:41][N:36]([CH3:35])[CH2:37][CH2:38]4)[O:8][CH:9]=3)=[CH:22][CH:23]=[N:24]2)=[CH:29][CH:28]=1

Participants

Conditions

Temperature: 45 °C

Procedure

Methanesulfonic acid 4-oxo-5-[5-(7-trifluoromethyl-quinolin-4-yloxy)-pentyloxy]-4H-pyran-2-ylmethyl ester 17 (130 mg, 0.26 mmol) was dissolved in dichloromethane (5 mL). 1-Methyl-piperazine (75 μL, 0.67 mmol) was added via syringe. The mixture was stirred at 45° C. for 3 h. After cooling to room temperature CH2Cl2 (75 ml) was added and the mixture was washed with NaHCO3 10% (3×50 mL) and 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=9:1. 5-(5-(7-(Trifluoromethyl)quinolin-4-yloxy)pentyloxy)-2-((4-methylpiperazin-1-yl)methyl)-4H-pyran-4-one EHT 0079 was obtained (30 mg, 23% yield) as a yellow oil.

Workup

additionwas added
washthe mixture was washed with NaHCO3 10% (3×50 mL) and 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-410be32db58a4eadb1781021808a1e92
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514432B2

Reaction notes

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