반응 #2148363

반응 방정식

(S)-Tetrahydrofuran-2-carboxylic acid

HATU

DIPEA

17

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

→

(S)-1,7-dimethyl-3-(2-methyl-5-(5-(tetrahydrofuran-2-yl)-1,2,4-oxadiazol-3-ylamino)phenyl)-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

(S)-Tetrahydrofuran-2-carboxylic acid (75.7 mg, 0.65 mmol), HATU (247 mg, 0.65 mmol), and DIPEA (0.11 mL, 0.65 mmol) were stirred in dry DMF (6 mL) for 1 h before 17 (200 mg, 0.59 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 (S)-1,7-dimethyl-3-(2-methyl-5-(5-(tetrahydrofuran-2-yl)-1,2,4-oxadiazol-3-ylamino)phenyl)-1,6-naphthyridin-2(1H)-one (A77) as a solid. 1H NMR (400 MHz, d4-MeOH) δ 9.07 (s, 1H), 8.04 (s, 1H), 7.91 (s, 1H), 7.45 (d, J=4 Hz, 1H), 7.36 (dd, J=8, 4 Hz, 1H), 7.25 (d, J=4 Hz, 1H), 5.10 (dd, J=8, 4 Hz, 1H), 4.03 (dd, J=12, 8 Hz, 1H), 3.96 (dd, J=12, 8 Hz, 1H), 3.83 (s, 3H), 2.85 (s, 3H), 2.41-2.34 (m, 1H), 2.28-2.20 (m, 1H), 2.16 (s, 3H), 2.12-2.03 (m, 2H). MS m/z 417.5, 418.5 (M+1).

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