반응 #2148352

반응 방정식

2,2-difluoropropanoic acid

HATU

DIPEA

Na2SO4

17

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

→

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

용매

DMF

반응 조건

후처리

1. 1
   기타The consumption of 17
2. 2
   여과Solid was filtered off
3. 3
   기타the residue was purified with preparative HPLC

실험 절차

To a solution of 2,2-difluoropropanoic acid (11 mg, 0.1 mmol), HATU (42 mg, 0.11 mmol) and DIPEA (15 mg, 0.12 mmol) in dry DMF (0.5 mL) at rt in the presence of anhydrous Na2SO4 (71 mg, 0.5 mmol) were added 17 (33.7 mg, 0.10 mmol) slowly. The consumption of 17 was determined to be completed by LC/MS. The mixture was heated at 100° C. for 2 h. Solid was filtered off and the residue was purified with preparative HPLC to yield 3-(5-(5-(1,1-difluoroethyl)-1,2,4-oxadiazol-3-ylamino)-2-methylphenyl)-1,7-dimethyl-1,6-naphthyridin-2(1H)-one (A54). 1H NMR (400 MHz, DMSO-d6) δ 10.27 (s, 1H), 9.00 (s, 1H), 8.03 (s, 1H), 7.70 (s, 1H), 7.42 (d, J=8.4 Hz, 1H), 7.33 (s, 1H), 7.27 (d, J=8.0 Hz, 1H), 2.70 (s, 3H), 2.51 (s, 3H), 2.16 (t, J=19.6 Hz, 3H), 2.10 (s, 3H). MS m/z 412.2 (M+1).

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