Diethyl Ether → HCID 59000775, compound

HRID 1594011Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C([O:9][C:10]([C:12]1[C:13]([C:36](OCC)=[O:37])=[C:14]([CH2:33][CH2:34][CH3:35])[N:15]2[C:20]=1[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:18][C:17]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[N:16]2)=O)C.CCOCC>C1COCC1>[OH:9][CH2:10][C:12]1[C:13]([CH2:36][OH:37])=[C:14]([CH2:33][CH2:34][CH3:35])[N:15]2[C:20]=1[C:19]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)=[CH:18][C:17]([N:27]1[CH2:32][CH2:31][O:30][CH2:29][CH2:28]1)=[N:16]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of lithium aluminum hydride (118 mg, 3.11 mmol) in THF (10 mL) was added 2-morpholino-4-yl-4-phenyl-7-propyl-pyrrolo [1,2-b]pyridazine-5,6-dicarboxylic acid diethyl ester (15) (242 mg, 0.52 mmol). The reaction mixture was heated at reflux for 1 h. After cooling to 0° C., Et2O (10 mL) was added and an excess reagent in the reaction mixture was quenched by brine. The resulting precipitate was removed by filtration. The filtrate was dried over Na2SO4 and concentrated in vacuo to provide the title compound. 1H NMR (DMSO-d6) δ 0.92 (t, J=7.2 Hz, 3H), 1.63-1.71 (m, 2H), 2.91 (t, J=7.2 Hz, 2H), 3.40 (br t, J=5.0 Hz, 4H), 3.72 (br t, J=5.0 Hz, 4H), 4.05 (d, J=5.0 Hz, 2H), 4.22 (t, J=5.0 Hz, 1H), 4.55 (d, J=5.1 Hz, 2H), 4.61 (t, J=5.1 Hz, 1H), 6.34 (s, 1H), 7.46-7.48 (m, 3H), 7.53-7.56 (m, 2H). Mass Spectrum (ESI+) m/e=364 (M−OH).

Workup

temperatureThe reaction mixture was heated
temperatureat reflux for 1 h
customan excess reagent in the reaction mixture was quenched by brine
customThe resulting precipitate was removed by filtration
dry with materialThe filtrate was dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-eeb5a251aeec461383f61faf19597126
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07300932B2

Reaction notes

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