Hydrochloric Acid → HCID 67345140, compound

A solution of 2,2-dimethyl-5-(methylsulfanyl-thiophene-3-ylamino-methylene)-[1,3]dioxane-4,6-dione (27.83 g, 92.8 mmol) in DCM/MeOH (4:1, 120 mL) was added to a solution of 1,3-diaminopropane (54.9 g, 138 mmol) in DCM/MeOH (4:1, 140 mL) (cooled in an ice bath) over one hour. The ice bath was removed after addition was complete. The reaction was stirred for 2 h at ambient temperature, then diluted with DCM (100 mL) and the resultant organic solution was washed with water (60 mL X 4) and brine (60 mL). Then, acetic anhydride (11 mL, 116 mmol) and trimethylamine (16 mL, 111.4 mmol) was added to the above organic solution and stirred for 30 min. An aqueous work-up with 1N HCl, then NaHCO3 (saturated) and then brine was performed. The organic was dried with MgSO4, filtered and volatile solvents removed in vacuo to afford the desired product N-(3-{[(2,2-dimethyl-4,6-dioxo-[1,3]dioxan-5-ylidene)-(thiophen-3-ylamnio)-ethyl]-amino}-propyl)-acetamide (30.7 g, 84%) as a brown oil, which was used in the next step without purification. 1H NMR (CDCl3): 11.3 (1H, br s), 10.0 (1H, br s), 7.33 (1H, dd, J=3.2, 5 MHz), 7.07 (1H, d, J=3.2 MHz), 6.98 (1H, d, J=5), 3.20 (2H, quart, J 6.4 MHz), 3.90 (1H, quart. J=6.8 MHz), 1.94 (3H, s), 1.73 (6H, s), 1.68 (2H, m) ppm.

1. customThe ice bath was removed
2. additionafter addition
3. additiondiluted with DCM (100 mL)
4. washthe resultant organic solution was washed with water (60 mL X 4) and brine (60 mL)
5. stirringstirred for 30 min
6. dry with materialThe organic was dried with MgSO4
7. filtrationfiltered
8. customvolatile solvents removed in vacuo

ORD record

ord-007aaaa62e2f49daa6e8292900e8205c

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07994192B2