tert-Butyl (3-aminopropyl)carbamate → (3-{[(3-Benzyl-5-chloro-4-oxo-3,4-dihydro-pyrrolo[2,1-f][1,2,4]triazin-2-yl)-cyclopropyl-methyl]-amino}-propyl)-carbamic acid tert-butyl ester

(3-Amino-propyl)-carbamic acid tert-butyl ester (Fluka, 0.527 mL, 3.02 mmol) was added to a solution of 3-benzyl-5-chloro-2-(chloro-cyclopropyl-methyl)-3H-pyrrolo[2,1-f][1,2,4]triazin-4-one (0.35 g, 1.01 mmol) in NMP (3.3 mL) at room temperature. The reaction mixture was degassed with N2 and then stirred at 100° C. for 12 h. The reaction mixture was cooled to room temperature and the crude product was purified by loading directly onto a reverse phase C-18 HPLC with a 30 min gradient eluting with 45–90% aqueous methanol with 0.1% TFA to afford the title compound (0.397 g, 81%) as a solid: 1H NMR (DMF-d7) 7.74 (m, 1H), 7.35–7.49 (m, 5H), 6.85 (m, 2H), 5.85 (m, 1H), 5.45 (m, 1H), 3.15–3.25 (m, 3H), 2.70–2.85 (m, 2H), 2.55 (br m, 1H), 1.55–165 (m, 2H), 1.47 (s, 9H), 1.40 (br m, 1H), 0.65–0.75 (m, 1H), 0.41–0.46 (m, 2H), 0.15 (br m, 1H); MS (ESI+) 486 (M++H); HRMS (ESI+) calculated: 486.2272 (M++H). found: 486.2256 (M++H).

1. customThe reaction mixture was degassed with N2
2. temperatureThe reaction mixture was cooled to room temperature
3. customthe crude product was purified by loading directly onto a reverse phase C-18 HPLC with a 30 min
4. washgradient eluting with 45–90% aqueous methanol with 0.1% TFA

ORD 기록

ord-fe5e5fc8acfa49eb96a7e1182d4e2925

출처 데이터셋

uspto-grants-2006_04

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07030118B2