Trifluoroacetic acid → HCID 136629508, compound

A solution of 36 (1.8 g, 3.6 mmol) in a mixture of TFA (60 ml) and water (20 ml) was kept at room temperature for 2 days until almost no starting material was found by HPLC analysis. The reaction was concentrated, co-evaporated with water (3×100 ml) and re-dissolved in ˜5 ml of acetonitrile. Ethyl ether (˜50 ml) was added to precipitate 0.84 g of 37 as a TFA salt. The salt was dissolved in ˜7 ml of ethanol, treated with 0.5 ml of triethylamine and allowed to crystallize at −20° C. for 2 hrs. The crystals were collected by filtration, washed with ethyl ether and dried in vacuo to afford 0.64 g (70%) of 37 as a white solid. 1H NMR (DMSO-d6): δ 10.55 (s, 1H), 7.63 (s, 1H), 6.46 (s, 2H), 4.63 (d, J=5 Hz, 1H), 4.55 (t, J=5 Hz, 1H), 3.97 (d, J=7.5 Hz, 2H), 3.64 (m, 1H), 3.41 (m, 2H), 1.92 (m, 1H), 1.10 (d, J=6.3 Hz, 3H).

1. concentrationThe reaction was concentrated, co-evaporated with water (3×100 ml)
2. dissolutionre-dissolved in ˜5 ml of acetonitrile
3. additionEthyl ether (˜50 ml) was added
4. customto precipitate 0.84 g of 37 as a TFA salt
5. dissolutionThe salt was dissolved in ˜7 ml of ethanol
6. additiontreated with 0.5 ml of triethylamine
7. customto crystallize at −20° C. for 2 hrs
8. filtrationThe crystals were collected by filtration
9. washwashed with ethyl ether
10. customdried in vacuo

ORD record

ord-facac293392840bdb24649b21ec0040d

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169256B2