2-(Methyloxy)-4-[4-(4-morpholinyl)-1-piperidinyl]aniline → [7-(2-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[2-methoxy-4-(4-morpholin-4-yl-piperidin-1-yl)-phenyl]-amine

HRID 1262085Notes

Reaction equation

HRID 1262085 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N:9]2[CH2:14][CH2:13][CH:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH2:11][CH2:10]2)[CH:6]=[CH:5][C:4]=1[NH2:21].CS([C:25]1[N:30]=[CH:29][C:28]2=[CH:31][CH:32]=[C:33]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[S:40]([CH3:43])(=[O:42])=[O:41])[N:27]2[N:26]=1)=O>>[CH3:43][S:40]([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][C:34]=1[C:33]1[N:27]2[C:28]([CH:29]=[N:30][C:25]([NH:21][C:4]3[CH:5]=[CH:6][C:7]([N:9]4[CH2:14][CH2:13][CH:12]([N:15]5[CH2:20][CH2:19][O:18][CH2:17][CH2:16]5)[CH2:11][CH2:10]4)=[CH:8][C:3]=3[O:2][CH3:1])=[N:26]2)=[CH:31][CH:32]=1)(=[O:41])=[O:42]

Participants

3

Reactant 2

HCID 574161442-(Methyloxy)-4-[4-(4-morpholinyl)-1-piperidinyl]anilineHCID 667114062-Methanesulfinyl-7-(2-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66711055[7-(2-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[2-methoxy-4-(4-morpholin-4-yl-piperidin-1-yl)-phenyl]-amine

Conditions

Temperature
190 °C

Procedure

Following the procedure of example 532 (c), 2-Methoxy-4-(4-morpholin-4-yl-piperidin-1-yl)-phenylamine (0.095 g, 0.33 mmol) and 2-Methanesulfinyl-7-(2-methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (0.17 g, 0.51 mmol) were heated in the microwave at 190° C. for 3 hours. Purification by Gilson chromatography gave [7-(2-Methanesulfonyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[2-methoxy-4-(4-morpholin-4-yl-piperidin-1-yl)-phenyl]-amine as a tan solid; MP: 111-112° C.; LCMS (m/e) 563 (M+1); 1H-NMR (DMSO-d6, 400 MHz) δ 8.94 (s, 1H), 8.16-8.14 (d, 1H, J=8.04 Hz), 7.887.85 (t, 1H, J=7.25 Hz), 7.807.60 (t, 1H, J=7.48 Hz), 7.707.68 (d, 1H, J=7.58 Hz), 7.60 (s, 1H), 7.43-7.41 (d, 1H, J=8.45 Hz), 6.94-6.92 (q, 2H, J=5.45 Hz), 6.56 (s, 1H), 6.21-6.19 (d, 1H, J=8.80 Hz), 5.75 (s, 1H), 3.76 (s, 3H), 3.62-3.58 (m, 4H), 3.01 (s, 3H), 2.88 (s, 3H), 2.61-2.55 (t, 1H), 2.23 (t, 1H), 1.86-1.83 (d, 2H, J=11.77 Hz), 1.48-1.45 (q, 2H, J=11.36).

Workup

  1. customPurification by Gilson chromatography

Sources & evidence

ORD record
ord-99026691775b4c92b60923435726a3cc
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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