2-Methoxyethanol → N-[7-(3-Chloro-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-N',N'-dimethyl-benzene-1,3-diamine

HRID 1261930노트

반응식

HRID 1261930 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]3[C:11]([CH:12]=[N:13][C:14](S(C)=O)=[N:15]3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)C(C)C)(C)C.[CH3:29][N:30]([CH3:38])[C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([NH2:37])[CH:32]=1.COCCO>>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[N:16]3[C:11]([CH:12]=[N:13][C:14]([NH:37][C:33]4[CH:34]=[CH:35][CH:36]=[C:31]([N:30]([CH3:38])[CH3:29])[CH:32]=4)=[N:15]3)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 4

HCID 80192-MethoxyethanolHCID 76084N,N-dimethyl-m-phenylenediamineHCID 81531DiisopropylethylamineHCID 66710773HCID 66710773, 화합물

생성물 1

HCID 66710978N-[7-(3-Chloro-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-N',N'-dimethyl-benzene-1,3-diamine수율 3.9%

반응 조건

온도
180 °C

실험 절차

7-(3-Chloro-phenyl)-2-methanesulfinyl-pyrrolo[2,1-f][1,2,4]triazine (76.2 mg, 0.000261 mol), N,N-Diisopropylethylamine (0.0682 mL, 0.000392 mol) and N,N-Dimethyl-benzene-1,3-diamine (71.1 mg, 0.000522 mol) were dissolved in 2-Methoxyethanol (1.83 mL, 0.0232 mol) and the reaction was heated at 180° C. 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 3.73 mg of N-[7-(3-Chloro-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-N′,N′-dimethyl-benzene-1,3-diamine as a lyophilated powder. (M+H)=364.11. 1H NMR (400 MHz, CDCl3) δ 9.08 (s, 1H), 8.37 (d, 1H, J=9.60 Hz), 8.10 (s, 1H), 7.89 (d, 1H, J=7.58 Hz), 7.44 (m, 3H), 7.20 (d, 1H, J=4.80 Hz), 7.03 (d, 1H, J=4.54 Hz), 6.61 (m, 2H), 3.11 (s, 6H).

후처리

  1. customconsumption of starting material
  2. customthe product was isolated
  3. custompurified by Gilson prep HPLC

출처 및 근거

ORD 기록
ord-43f0daa2fec84b7c86d0f06e0ba35180
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471005B2

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