반응 #2148347

반응 방정식

2-Hydroxy-2-methylpropanoic acid

HATU

DIPEA

17

(E)-1-(3-(1,7-dimethyl-2-oxo-1,2-dihydro-1,6-naphthyridin-3-yl)-4-methylphenyl)-2-hydroxyguanidine

→

3-(5-(5-(2-hydroxypropan-2-yl)-1,2,4-oxadiazol-3-ylamino)-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one

용매

DMF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added at rt
2. 2
   온도After cooling
3. 3
   여과filtration
4. 4
   기타the mixture was purified by preparative LC/MS

실험 절차

2-Hydroxy-2-methylpropanoic acid (16.1 mg, 0.15 mmol), HATU (59 mg, 0.15 mmol), and DIPEA (0.027 mL, 0.15 mmol) were stirred in dry DMF (3 mL) for 1 h before 17 (50 mg, 0.14 mmol) was added at rt. The stirring was continued for 1 h before it was heated at 100° C. for 5 h. After cooling and filtration, the mixture was purified by preparative LC/MS to give 3-(5-(5-(2-hydroxypropan-2-yl)-1,2,4-oxadiazol-3-ylamino)-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one (A32) as a solid. 1H NMR (400 MHz, d4-MeOH) δ 8.90 (s, 1H), 7.94 (s, 1H), 7.81 (s, 1H), 7.62 (dd, J=8, 4 Hz, 1H), 7.52 (d, J=8, 4 Hz, 1H), 7.35 (d, J=4 Hz, 1H), 7.26 (dd, J=8, 4 Hz, 1H), 7.14 (d, J=8 Hz, 1H), 3.79 (s, 3H), 2.75 (s, 3H), 2.06 (s, 3H), 1.35 (m, 6H). MS m/z 406.2 (M+1).

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