Trifluoroacetic acid → 4-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-((1R,2S)-2-aminocyclohexylamino)pyridazine-3-carboxamide

To a solution of tert-butyl (1S,2R)-2-(5-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-carbamoylpyridazin-3-ylamino)cyclohexylcarbamate (79 mg, 160 μmol) in dichloromethane (2.5 mL) was added trifluoroacetic acid (364 mg, 246 μL, 3.19 mmol) and the mixture stirred at room temperature for 16 h. The mixture was diluted with dichloromethane and 1 N NaOH (2 mL), and then washed with NaHCO3 and brine. The organic layer was dried over MgSO4, then filtered and concentrated in vacuo. The mixture was dissolved in ethanol and concentrated (3×). The residue obtained was triturated with ether and finally filtered to give 4-(6-(2H-1,2,3-triazol-2-yl)pyridin-2-ylamino)-6-((1R,2S)-2-aminocyclohexylamino)pyridazine-3-carboxamide (5 mg, 10.8 μmol, 7%) as a light brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.12 (s, 1H), 8.46 (s, 1H), 8.38 (s, 2H), 7.99 (t, J=8.1 Hz, 1H), 7.80 (s, 1H), 7.62 (d, J=8.1 Hz, 1H), 7.11 (d, J=8.2 Hz, 1H), 6.94 (s., 1H), 1.35-1.85 (m, 8H), 1.46 (m, 2H); MS (EI/CI) m/z: 395.1 [M+H].

1. washwashed with NaHCO3 and brine
2. dry with materialThe organic layer was dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. dissolutionThe mixture was dissolved in ethanol
6. concentrationconcentrated (3×)
7. customThe residue obtained
8. customwas triturated with ether
9. filtrationfinally filtered

ORD 기록

ord-8a87bdf42dd34ccaa9a94293ecb1884c

출처 데이터셋

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08901124B2