반응 #60895
ord-5db5d36b35084a36a13d99a10893518c
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후처리
- 1온도The reaction mixture was heated
- 2온도at reflux for 24 hours
- 3온도After heating for 5 days
- 4농축the reaction mixture was concentrated in vacuo
- 5workup.ADDITIONdiluted with saturated NaHCO3 solution (5 mL)
- 6추출then extracted with DCM (2×10 mL)
- 7건조The combined organics were dried (MgSO4)
- 8여과filtered
- 9농축concentrated in vacuo
- 10기타to give a brown residue which
- 11농축then concentrated in vacuo
- 12workup.ADDITIONdiluted with 2M NaOH (8 mL)
- 13추출extracted with DCM (1×20 mL)
- 14건조The organic layer was dried (MgSO4)
- 15여과filtered
- 16농축concentrated in vacuo
- 17기타giving a residue which
- 18기타was purified by flash chromatography on silica (2% MeOH/DCM)
실험 절차
N-Benzoyl-N-[2-(1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-yl]benzamide (Intermediate 96) (0.05 g) was dissolved/suspended in MeCN (5 mL), dimethylcarbamyl chloride (0.015 mL) added, then benzaldehyde (16 mg) and DIPEA (0.05 mL). The reaction mixture was heated at reflux for 24 hours then additional dimethylcarbamyl chloride (0.015 mL), benzaldehyde (16 mg) and DIPEA (0.05 mL) added. After heating for 5 days, the reaction mixture was concentrated in vacuo, diluted with saturated NaHCO3 solution (5 mL) then extracted with DCM (2×10 mL). The combined organics were dried (MgSO4), filtered and concentrated in vacuo to give a brown residue which was dissolved in MeOH (2 mL)/concentrated aqueous NH3 (2 mL). The reaction mixture was heated at 55° C. for 1 hours then concentrated in vacuo, diluted with 2M NaOH (8 mL) and extracted with DCM (1×20 mL). The organic layer was dried (MgSO4), filtered, concentrated in vacuo giving a residue which was purified by flash chromatography on silica (2% MeOH/DCM) to give the title compound as a colourless solid (0.033 g, 68%);