Morpholine → HCID 10347887, compound

HRID 2108865Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[C:28](=[O:29])[CH:27]=[C:26]([CH2:30]OS(C)(=O)=O)[O:25][CH:24]=1)=[CH:13][CH:12]=[C:11]([C:36]([F:39])([F:38])[F:37])[CH:10]=2)=[O:5])[CH3:2].[NH:40]1[CH2:45][CH2:44][O:43][CH2:42][CH2:41]1>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][C:23]1[C:28](=[O:29])[CH:27]=[C:26]([CH2:30][N:40]3[CH2:45][CH2:44][O:43][CH2:42][CH2:41]3)[O:25][CH:24]=1)=[CH:13][CH:12]=[C:11]([C:36]([F:39])([F:38])[F:37])[CH:10]=2)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 45 °C

Procedure

4-[5-(6-Methanesulfonyloxymethyl-4-oxo-4H-pyran-3-yloxy)-pentyloxy]-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester 18 (123 mg, 0.214 mmol) was dissolved in dichloromethane (3 mL). Morpholine (47.3 μL, 0.537 mmol) was added via syringe. The mixture was stirred at 45° C. for 3 h. CH2Cl2 (50 ml) was added and the solution 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=95:05. 4-[5-(6-Morpholin-4-ylmethyl-4-oxo-4H-pyran-3-yloxy)-pentyloxy]-7-trifluoromethyl-quinoline-3-carboxylic acid ethyl ester EHT 8935 was obtained (66 mg, 55%) as a colourless oil.

Workup

washthe solution 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-3bf24e764c7740d9a9cb747cf3275015
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514432B2

Reaction notes

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