Dimethylamine → HCID 53891503, compound

HRID 1762218Notes

Reaction equation

[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:7]=1[CH2:8][O:9][C:10]1[C:11]2[N:12]([C:16](CC#C)=[C:17]([CH3:19])[N:18]=2)[CH:13]=[CH:14][CH:15]=1)=[O:4].C=O.CNC>O1CCOCC1.O>[CH3:1][O:2][C:3]([NH:5][C:6]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:7]=1[CH2:8][O:9][C:10]1[C:11]2[N:12]([CH:16]=[C:17]([CH3:19])[N:18]=2)[CH:13]=[CH:14][CH:15]=1)=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 8-(2-methoxycarbonylamino-6-methylbenzyloxy)-2-methyl-3-(2-propynyl)imidazo[1,2-a]pyridine (230 mg) in 1.4-dioxane (4.6 ml) were added 36% formaldehyde (105 mg), 50% dimethylamine in water (142 mg) and cuprous chloride (12.5 mg). After the mixture was stirred at 50° C. for 5 hours, 1.4-dioxane was evaporated under reduced pressure. The resultant residue was dissolved in chloroform (20 ml) and insoluble material was filtered off. The filtrate was washed with an aqueous solution of sodium bicarbonate and water in turn, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was recrystallized from a mixture of ethyl acetate and n-hexane to give 3-(4-N,N-dimethylamino-2-butynyl(-8-(2-methoxycarbonylamino-6-methylbenzyloxy)-2-methylimidazo-[1,2-a]pyridine (175 mg).

Workup

custom1.4-dioxane was evaporated under reduced pressure
dissolutionThe resultant residue was dissolved in chloroform (20 ml)
filtrationinsoluble material was filtered off
washThe filtrate was washed with an aqueous solution of sodium bicarbonate and water in turn
dry with materialdried over magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was recrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record: ord-9a4c090ae90c441f97e9abc2102bed77
Source dataset: uspto-grants-1989_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04831041

Reaction notes

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