3-Methoxy-4-(1-methylpiperidin-4-yl)aniline → [3-Methoxy-4-(1-methyl-piperidin-4-yl)-phenyl]-[7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

HRID 1262143노트

반응식

HRID 1262143 반응식
[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:17]3[C:12]([CH:13]=[N:14][C:15](OS(C(F)(F)F)(=O)=O)=[N:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[CH3:26][O:27][C:28]1[CH:29]=[C:30]([NH2:41])[CH:31]=[CH:32][C:33]=1[CH:34]1[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]1>>[CH3:26][O:27][C:28]1[CH:29]=[C:30]([NH:41][C:15]2[N:14]=[CH:13][C:12]3=[CH:11][CH:10]=[C:9]([C:6]4[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[N:17]3[N:16]=2)[CH:31]=[CH:32][C:33]=1[CH:34]1[CH2:35][CH2:36][N:37]([CH3:40])[CH2:38][CH2:39]1

참가 물질

3

반응물 2

HCID 574160883-Methoxy-4-(1-methylpiperidin-4-yl)anilineHCID 86661684Trifluoro-methanesulfonic acid 7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester

생성물 1

HCID 66711918[3-Methoxy-4-(1-methyl-piperidin-4-yl)-phenyl]-[7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

실험 절차

Trifluoro-methanesulfonic acid 7-(6-methoxy-pyridin-3-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl ester (0.138 g, 0.369 mmol) and 3-Methoxy-4-(1-methyl-piperidin-4-yl)-phenylamine (0.102 g, 0.461 mmol) were reacted in an analogous manner to Example 908D at room temp for 72 h. The reaction mixture was concentrated, taken up in EtOAc, and washed with brine. The EtOAc layer was dried, filtered over MgSO4, and concentrated. The resulting residue was purified by Gilson RP-HPLC and lyophilized. HPLC rt=2.455 min, purity=98%, LCMS=445.0 (M+H). 1H NMR (400 MHz, (D3C)2SO, δ, ppm): 9.47 (s, 1H), 9.29 (bs, 1H), 9.02 (s, 1H), 8.99 (d, 1H), 7.47 (s, 1H0, 7.23 (d, J=7.5 Hz, 1H), 7.17 (d, J=4.8 Hz, 1H), 7.03 (d, J=8.2 Hz, 1H), 7.17 (d, J=4.8 Hz, 1H), 7.03 (d, J=8.2 Hz, 1H), 6.98 (s, 1H), 6.96 A (d, J=4.1 Hz, 1H), 3.93 (s, 3H), 3.71 (s, 3H), 3.49 (d, J=11.7 Hz, 2H), 3.11-3.05 (m, 3H), 2.80 (d, J=4.0 Hz, 3H), 1.95-1.76 (m, 4H).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with brine
  3. dry with materialThe EtOAc layer was dried
  4. filtrationfiltered over MgSO4
  5. concentrationconcentrated
  6. customThe resulting residue was purified by Gilson RP-HPLC
  7. customHPLC rt=2.455 min, purity=98%, LCMS=445.0 (M+H)

출처 및 근거

ORD 기록
ord-bb6c3f3ace974d68805eb5a0f1ea029d
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471005B2

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