2-Amino-4-methylthiazole → 4-(methyl(pyridin-3-yl)amino)-N-(4-methylthiazol-2-yl)picolinamide

Compound 12 (0.1 g, 0.4 mmol, 1 eq), 4-methylthiazol-2-amine (60 mg, 0.53 mmol, 1.2 eq), 2-(1H-7-Azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (348 mg, 0.915 mmol, 2.10 eq), and DIEA (160 μL, 0.915 mmol, 2.10 eq) were dissolved in CH2Cl2 (5 mL) and DMF (1 mL) and stirred rt for 48 h. The reaction was diluted with CH2Cl2 and washed with water (1×). The organics were dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 35 mg (25%) of the title compound as a white solid: 1H NMR (400 MHz, CDCl3) δ 8.60 (d, J=2.3 Hz, 1H), 8.56 (dd, J=4.7, 1.1 Hz, 1H), 8.33 (d, J=4.8 Hz, 1H), 7.83 (ddd, J=8.2, 2.4, 1.5 Hz, 1H), 7.55 (dd, J=8.1, 4.7 Hz, 1H), 7.31 (s, 1H), 6.94-6.89 (m, 1H), 8.86 (s, 1H), 3.40 (s, 3H), 2.28 (s, 3H); [M+1]+: 326.2.

1. washwashed with water (1×)
2. dry with materialThe organics were dried (MgSO4)
3. filtrationfiltered
4. concentrationconcentrated in vacuo
5. customPurification by flash chromatography on silica gel

ORD 기록

ord-e5a1a21d7ad346c799ff4af692ed3456

출처 데이터셋

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08598345B2