Dimethylcarbamoyl Chloride → HCID 70980938, compound
Reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=2)[CH:7]=1.C(N(CC)CC)C.[CH3:23][N:24]([CH3:28])[C:25](Cl)=[O:26]>C1COCC1>[CH3:23][N:24]([CH3:28])[C:25](=[O:26])[NH:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[N:10]=2)[CH:7]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Ethyl 6-aminoimidazo[1,2-a]pyridine-2-carboxylate (0.975 mmol, 0.2 g) was dissolved in THF (10 ml). Triethylamine (2.92 mmol, 0.296 g) was added and the reaction mixture was cooled to 0° C. Dimethylcarbamyl chloride (1.462 mmol, 0.135 ml) was added carefully and the mixture was allowed to warm to ambient temperature with stirring. More of dimethylcarbamyl chloride (1.462 mmol, 0.135 ml) was added and the stirring continued for another hour. The solvent was evaporated, DCM was added and the resulting mixture was washed with NaHCO3 solution and water. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.066 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.31 (t, 3H), 2.95 (s, 6H), 4.29 (q, 2H), 7.39-7.44 (m, 1H), 7.50-7.54 (m, 1H), 8.41 (s, 1H), 8.54 (s, 1H), 8.89-8.93 (m, 1H).
Workup
- temperatureto warm to ambient temperature
- waitthe stirring continued for another hour
- customThe solvent was evaporated
- additionDCM was added
- washthe resulting mixture was washed with NaHCO3 solution and water
- customThe organic phase was dried
- filtrationfiltered
- customevaporated
- customThe crude product was purified by flash chromatography
Sources & evidence
- ORD record
- ord-256d8f6314cf4a20bbcc531c9230bd9b
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08921378B2
Reaction notes
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