HCID 68295331, compound → HCID 60198962, compound

To a solution of tert-butyl 3-(3,4-dichlorophenyl)-3-(2-(isopropylamino)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-7-carboxamido)propylcarbamate (89 mg, 0.17 mmol) in THF (5 mL) under N2 was added BH3.THF complex (0.36 mL, 0.36 mmol) and the reaction was heated at reflux under N2 for 19 h. The reaction was cooled to RT, quenched with MeOH (10 mL), and heated at reflux for 1 h. The reaction was concentrated, then partitioned between DCM (25 mL) and sat. aq. NaHCO3 (25 mL). The phases were separated, the aqueous phase extracted with DCM (25 ml). The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude product was purified on a preparative SiO2 TLC (1 mm) plate developed with MeOH/DCM/NH4OH (9/90/1) to afford 11 mg (15%) of I-111 as a white solid: 1H NMR (400 MHz, CDCl3) δ 8.07 (s, 1H), 7.36 (m, 2H), 7.13 (dd, 1H), 4.91 (m, 1H), 4.80 (d, 1H), 4.37 (m, 2H), 4.10 (m, 1H), 3.69 (m, 1H), 3.61 (m, 1H), 2.64-2.75 (m, 4H), 2.48 (s, 3H), 2.02 (m, 1H), 1.73 (m, 1H), 1.22 (dd, 6H); LRMS (APCI pos) m/e=451.1 (M+H).

1. temperaturethe reaction was heated
2. temperatureat reflux under N2 for 19 h
3. customquenched with MeOH (10 mL)
4. temperatureheated
5. temperatureat reflux for 1 h
6. concentrationThe reaction was concentrated
7. custompartitioned between DCM (25 mL) and sat. aq. NaHCO3 (25 mL)
8. customThe phases were separated
9. extractionthe aqueous phase extracted with DCM (25 ml)
10. dry with materialThe combined organic extracts were dried (MgSO4)
11. filtrationfiltered
12. concentrationconcentrated
13. customThe crude product was purified on a preparative SiO2 TLC (1 mm) plate
14. customto afford 11 mg (15%) of I-111 as a white solid

ORD record

ord-923097fa5b684203bc3e87a9d9ff420c

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09133187B2