Water → 6-Chloro-17-oxa-14-thia-2,4,8,24-tetraazatetracyclo[16.3.1.1(3,7).1(9,13)]tetracosa-1(22),3(24),4,6,9(23),10,12,18,20-nonaen-20-amine

Temperature

20 °C

A solution of 6-chloro-17-oxa-14-thia-2,4,8,24-tetraazatetracyclo[16.3.1.1(3,7).1(9,13)]tetracosa-1(22),3(24),4,6,9(23),10,12,18,20-nonaene-20-carboxylic acid (0.40 g, 0.95 mmol) in tetrahydrofuran (10 mL) at 0° C. was treated with triethylamine (0.53 mL, 3.8 mmol) and diphenylphosphonic acid (0.45 mL, 2.1 mmol) and stirred at 20° C. for 2 h. The reaction mixture was poured into water (50 mL) and ethyl acetate (150 mL). The ethyl acetate layer was separated, diluted with water (50 mL) and heated at 100° C. for 8 h. The reaction mixture was filtered and the organic layer from the filtrate was separated and washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to give the desired product as a crude yellow. This material was treated with ethyl acetate and filtered. The filtrate was concentrated to give the desired product (0.29 g, 78%) as a tan solid. LCMS for C18H17ClN5OS (M+H)+: m/z=385.9.

1. customThe ethyl acetate layer was separated
2. additiondiluted with water (50 mL)
3. temperatureheated at 100° C. for 8 h
4. filtrationThe reaction mixture was filtered
5. customthe organic layer from the filtrate was separated
6. washwashed with brine (50 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationfiltered
9. customevaporated

ORD record

ord-8368a85b6b3c463eb7e6e6ee7e4e47ab

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871753B2