1-Methylpiperazine → 5-{4-[(4-Methylpiperazin-1-yl)methyl]benzamido}-2-(naphthalen-2-ylamino)thiazole-4-carboxamide

To a mixture of 5-amino-2-(naphthalen-2-ylamino)thiazole-4-carboxamide (0.50 g, 1.76 mmol) and. N,N-diisopropylethylamine (0.3 mL, 1.94 mmol) in DMA (30 mL) was added 4-chloromethylbenzoyl chloride (0.37g, 1.94 mmol) at 0° C. The mixture was stirred for 3 hrs at rt. Then 1-methylpiperazine (0.1 mL, 0.95 mmol) was added to the mixture (0.083 g in 5 mL DMA), and the mixture was stirred for 16 hrs at rt. The reaction mixture was diluted with ethyl acetate (150 mL), washed with water, and dried over Na2SO4. The solvent was evaporated under reduced pressure, and the crude residue was purified by silica gel column chromatograph eluted with 5% MeOH in DCM to give 0.010 g (11% yield) of the titled compound.

1. stirringthe mixture was stirred for 16 hrs at rt
2. washwashed with water
3. dry with materialdried over Na2SO4
4. customThe solvent was evaporated under reduced pressure
5. customthe crude residue was purified by silica gel column chromatograph
6. washeluted with 5% MeOH in DCM

ORD record

ord-954b9c94b4784ce980d33420695ee65d

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09102637B2