3-(4-Methylpiperazin-1-yl)aniline → HCID 66712562, compound

HRID 1262439Notes

Reaction equation

HRID 1262439 reaction equation
[C:1]([O:5][CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[N:21]3[C:16]([CH:17]=[N:18][C:19](O)=[N:20]3)=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([C:30]2[CH:31]=[C:32]([CH:34]=[CH:35][CH:36]=2)[NH2:33])[CH2:26][CH2:25]1>>[C:1]([O:5][CH2:6][C:7]1[CH:8]=[C:9]([C:13]2[N:21]3[C:16]([CH:17]=[N:18][C:19]([NH:33][C:32]4[CH:34]=[CH:35][CH:36]=[C:30]([N:27]5[CH2:26][CH2:25][N:24]([CH3:23])[CH2:29][CH2:28]5)[CH:31]=4)=[N:20]3)=[CH:15][CH:14]=2)[CH:10]=[CH:11][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 115646133-(4-Methylpiperazin-1-yl)anilineHCID 178450409HCID 178450409, compound

Product 1

HCID 66712562HCID 66712562, compoundYield 45%

Procedure

Analogous to Example 1510b, 7-(3-tert-Butoxymethyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ol (109 mg, 0.37 mmol) and 3-(4-Methylpiperazin-1-yl)aniline (0.0878 g, 0.459 mmol) were reacted to afford [7-(3-tert-Butoxymethyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-[3-(4-methyl-piperazin-1-yl)-phenyl]-amine (78 mg, 45%). LCMS: 471 (M+H); 1H-NMR (DMSO-d6): 9.26 (s, 1H), 9.26 (s, 1H), 8.97 (s, 1H), 8.08 (s, 1H), 7.99 (d, 1H, J=7.83 Hz), 7.46 (t, 1H, J=7.83 Hz), 7.35 (d, 1H, J=7.83 Hz), 7.27 (m, 2H), 7.13 (m, 2H), 6.95 (d, 1H, J=4.38 Hz), 6.57 (d, 1H, J=8.50 Hz), 4.48 (s, 2H), 3.01 (s, 4H), 2.40 (s, 4H), 2.22 (s, 3H), 1.22 (s, 9H).

Sources & evidence

ORD record
ord-156bb953e0fe42e181acfe8f9ed37674
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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