Dimethylformamide dimethyl acetal → (2E)-1-(1,3-diethyl-1H-indazol-6-yl)-3-(dimethylamino)prop-2-en-1-one

HRID 2240181Notes

Reaction equation

CO[CH:3](OC)[N:4]([CH3:6])[CH3:5].[CH2:9]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20](=[O:22])[CH3:21])[CH:18]=2)[C:13]([CH2:23][CH3:24])=[N:12]1)[CH3:10]>CN(C)C=O>[CH2:9]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20](=[O:22])/[CH:21]=[CH:3]/[N:4]([CH3:5])[CH3:6])[CH:18]=2)[C:13]([CH2:23][CH3:24])=[N:12]1)[CH3:10]

Participants

Conditions

Temperature: 120 °C

Procedure

1,1-dimethoxy-N,N-dimethylmethanamine (0.891 g, 0.0075 mol) was added to a solution of 1-(1,3-Diethyl-1H-indazol-6-yl)-ethanone (0.187 mg, 8.64 mmol) in N,N-dimethylformamide (8 mL), and the resulting mixture was shaken at 120° C. for 16 hours. 1,1-dimethoxy-N,N-dimethylmethanamine (0.618 g, 0.0052 mol) was added, and the reaction was refluxed at 140° C. for a further 16 hours. The solvent was removed in vacuo, and the residue extracted with ethyl acetate (30 mL) and water (10 mL). The aqueous layer was re-extracted with ethyl acetate (30 mL). The organic layers were combined, dried, filtered and concentrated. The resulting crude product was purified by silica-gel chromatography, using an eluent gradient of 0.25-0.5% methanol in dichloromethane (mobile phase contained 0.5% ammonium hydroxide solution) to afford 35 mg of (2E)-1-(1,3-diethyl-1H-indazol-6-yl)-3-(dimethylamino)prop-2-en-1-one.

Workup

temperaturethe reaction was refluxed at 140° C. for a further 16 hours
customThe solvent was removed in vacuo
extractionthe residue extracted with ethyl acetate (30 mL) and water (10 mL)
extractionThe aqueous layer was re-extracted with ethyl acetate (30 mL)
customdried
filtrationfiltered
concentrationconcentrated
customThe resulting crude product was purified by silica-gel chromatography

Sources & evidence

ORD record: ord-d978f3b4e3b243958e085117ec0c218a
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07723348B2

Reaction notes

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