Dimethylformamide → HCID 86591942, compound

HRID 1676856Notes

Reaction equation

[CH2:1]([N:5]1[C:9](Cl)=[C:8]([Cl:11])[N:7]=[C:6]1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[CH2:2][CH2:3][CH3:4].CN([CH:21]=[O:22])C>C1COCC1>[CH2:1]([N:5]1[C:9]([CH:21]=[O:22])=[C:8]([Cl:11])[NH:7][CH:6]1[N:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: -78 °C

Procedure

N-BuLi (12.1 mL, 19.3 mmol, 1.6M in hexane) at 78° C. is added to a solution of 4-(1-butyl-4,5-dichloro-1H-imidazol-2-yl)-morpholine (3.48 g, 12.5 mmol) in anhydrous THF (50 mL) over a 30 minute period. After stirring for 2 hours at −78° C., anhydrous DMF (3 mL) is added at −78° C. Then the reaction mixture is allowed to warm to room temperature over a 2 hour period. The reaction is then quenched with water. The reaction mixture is extracted with ethyl acetate and dried over MgSO4. The extract is evaporated in vacuo to dryness and purified by flash column chromatography on silica gel using a mixture of hexane-ethyl acetate (4:1 to 3:1) as eluent to give 1-butyl-4-chloro-2-morpholin-4-yl-3H-imidazole-5-carbaldehyde as a colorless oil. 1HNMR (CDCl3) δ 9.59 (1H, s), 4.06 (2H, t, J=7.1 Hz), 3.78 (4H, t, J=4.6 Hz), 3.15 (4H, t, J=4.6 Hz), 1.60-1.70 (2H, m), 1.19-1.30 (2H, m), 0.90 (3H, t, J=7.3 Hz).

Workup

temperatureto warm to room temperature over a 2 hour period
customThe reaction is then quenched with water
extractionThe reaction mixture is extracted with ethyl acetate
dry with materialdried over MgSO4
customThe extract is evaporated in vacuo to dryness
custompurified by flash column chromatography on silica gel using
additiona mixture of hexane-ethyl acetate (4:1 to 3:1) as eluent

Sources & evidence

ORD record: ord-39367920906c4adea2ca6851c8afc2e7
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08007767B2

Reaction notes

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