Trifluoroacetic acid → HCID 73055151, Verbindung

To a solution of tert-butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzoyl)piperazine-1-carboxylate (A26) (0.182 g, 0.297 mmol) in DCM (4 mL) was added TFA (1 mL) and the resulting mixture was stirred at room temperature for 16 hours. The volatiles were removed in vacuo and the residue partitioned between EtOAc (10 mL) and 2 M aqueous NaOH (10 mL). The aqueous layer was extracted with EtOAc (2×10 mL) then the combined organic fractions were washed with water (10 mL), brine (10 mL) and dried over MgSO4. The volatiles were removed in vacuo to give a yellow solid, which was suspended in cyclohexane and then filtered to give the title compound 6 as a white solid (0.132 g, 87%); 1H NMR (400 MHz, d4-MeOH) δ 8.62 (s, 1H), 7.83 (d, J=8.7 Hz, 2H), 7.42 (d, J=8.8 Hz, 2H), 7.27 (d, J=6.3 Hz, 1H), 7.23-7.15 (m, 3H), 3.68 (s, 2H), 3.82-3.46 (m, 4H), 3.23-3.15 (m, 2H), 3.12 (dd, J=9.8, 5.4 Hz, 2H), 3.02-2.71 (m, 4H). LCMS-A: rt 4.676 min; m/z 513.3 [M+H]+.

1. customThe volatiles were removed in vacuo
2. customthe residue partitioned between EtOAc (10 mL) and 2 M aqueous NaOH (10 mL)
3. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
4. washthe combined organic fractions were washed with water (10 mL), brine (10 mL)
5. dry with materialdried over MgSO4
6. customThe volatiles were removed in vacuo
7. customto give a yellow solid, which
8. filtrationfiltered

ORD-Eintrag

ord-eb3f008ac60e4015be2ef3c6aeaedf1a

Quelldatensatz

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09266864B2