[7-(2-Methoxy-phenyl)-5-vinyl-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine → [5-Ethyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

HRID 1261903노트

반응식

HRID 1261903 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]2[C:12]([CH:13]=[N:14][C:15]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([N:25]4[CH2:30][CH2:29][N:28]([CH3:31])[CH2:27][CH2:26]4)=[CH:21][CH:20]=3)=[N:16]2)=[C:11]([CH:32]=[CH2:33])[CH:10]=1>C(O)C.[Ni]>[CH2:32]([C:11]1[CH:10]=[C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[N:17]2[C:12]=1[CH:13]=[N:14][C:15]([NH:18][C:19]1[CH:20]=[CH:21][C:22]([N:25]3[CH2:26][CH2:27][N:28]([CH3:31])[CH2:29][CH2:30]3)=[CH:23][CH:24]=1)=[N:16]2)[CH3:33]

참가 물질

4

반응물 1

HCID 66711513[7-(2-Methoxy-phenyl)-5-vinyl-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine

생성물 1

HCID 66711526[5-Ethyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine수율 36%

시약·촉매·용매 2

HCID 935Nickel촉매HCID 702Ethanol용매2회

실험 절차

Into a par bottle, [7-(2-Methoxy-phenyl)-5-vinyl-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine (50.00 mg, 0.0001135 mol), and Ethanol (20 mL, 0.3 mol) were added. Raney-Nickel (0.9:0.1, Nickel:Aluminum, 10 mg, 0.0002 mol) was washed with Ethanol prior to adding to the reaction mixture. The mixture was evacuated and charged with hydrogen at 30 pSi. The reaction was shaken on the parr at 30 pSi for one hour. The solid was filtered through Celite. The organic was evaporated under vacuum to give a yellow solid. The solid was purified via ISCO column chromatography with DCM and MeOH as eluant (0 to 10% methanol). The collected fractions afforded [5-Ethyl-7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[4-(4-methyl-piperazin-1-yl)-phenyl]-amine as a yellow solid (18 mg, 36%). MP 154-156° C. LCMS (E/I+) 443.31 (M+H). NMR 1H (DSMO-d6)-9.05 (s, 1H), 8.92 (s, 1H), 7.80 (dd, 1H, JJ=1.57, 6.50 Hz), 7.55 (d, 2H, J=8.96 Hz), 7.43 (dt, 1H, JJ=1.60, 7.00 Hz), 7.20 (d, 1H, J=8.40) 7.10 (t, 1H, J=7.57 Hz, 6.73-6.85 (m, 3H), 3.79 (s, 3H), 3.02 (t, 4H, J=4.60), 2.83 (q, 2H, JJ=7.52, 7.56 Hz), 2.44 (t, 4H, J=5.84), 2.21 (s, 3H), 1.28 (t, 3H, J=7.56 Hz).

후처리

  1. additionto adding to the reaction mixture
  2. customThe mixture was evacuated
  3. additioncharged with hydrogen at 30 pSi
  4. filtrationThe solid was filtered through Celite
  5. customThe organic was evaporated under vacuum
  6. customto give a yellow solid
  7. customThe solid was purified via ISCO column chromatography with DCM and MeOH as eluant (0 to 10% methanol)

출처 및 근거

ORD 기록
ord-430d19be568e4686be60a5ff0fe6bd13
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471005B2

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