Methanesulfonic Acid → 5-[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1,3-dihydro-indol-2-one

反応式

CS([C:4]1[N:9]=[CH:8][C:7]2=[CH:10][CH:11]=[C:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[O:19][CH3:20])[N:6]2[N:5]=1)=O.CS(O)(=O)=O.[NH2:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][C:31](=[O:36])[CH2:30]2.COCC(O)C>>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]1[N:6]2[C:7]([CH:8]=[N:9][C:4]([NH:26][C:27]3[CH:28]=[C:29]4[C:33](=[CH:34][CH:35]=3)[NH:32][C:31](=[O:36])[CH2:30]4)=[N:5]2)=[CH:10][CH:11]=1

参加物

反応物 4

HCID 6395Methanesulfonic Acid

HCID 79001-Methoxy-2-propanol

HCID 27732135-Amino-2-oxindole

HCID 667107912-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine

生成物 1

HCID 667111645-[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1,3-dihydro-indol-2-one収率 5.6%

実験手順

2-Methanesulfinyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (75.0 mg, 0.000261 mol), Methanesulfonic acid (0.03388 mL, 0.0005220 mol) and [B] 5-Amino-1,3-dihydro-indol-2-one (77.3 mg, 0.000522 mol) were dissolved in 1-Methoxy-2-propanol (0.74 mL, 0.0076 mol) and the reaction was irradiated at 300 watts, 200° C. for 40 minutes or until HPLC showed consumption of starting material. The reaction mixture was then reduced en vacuo and the product was isolated and purified by Gilson prep HPLC to afford 5.40 mg of 5-[7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-1,3-dihydro-indol-2-one as a lyophilized powder. (M+H)=371.9. 1H NMR (400 MHz, DMSO, d6) δ 10.19 (s, 1H), 9.25 (s, 1H), 8.91 (s, 1H), 7.78 (d, 1H, J=7.53 Hz), 7.74 (s, 1H), 7.47 (t, 1H, J=7.53 Hz), 7.39 (d, 1H, J=7.88 Hz), 7.23 (d, 1H, J=8.09 Hz), 7.13 (t, 1H, J=7.28 Hz), 6.90 (dd, 2H, J=4.61, 6.41 Hz), 6.64 (d, 1H, J=8.37 Hz), 3.78 (s, 3H), 3.38 (s, 2H).