3-(4-Methylpiperazin-1-yl)aniline → [3-(4-Methyl-piperazin-1-yl)-phenyl]-[7-(1-methyl-1H-pyrazol-4-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine

HRID 1262156Notes

Reaction equation

HRID 1262156 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH:12]=[CH:13][CH:14]=2)[NH2:11])[CH2:4][CH2:3]1.CS([C:18]1[N:23]=[CH:22][C:21]2=[CH:24][CH:25]=[C:26]([C:27]3[CH:28]=[N:29][N:30]([CH3:32])[CH:31]=3)[N:20]2[N:19]=1)=O>>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[CH:9]=[C:10]([NH:11][C:18]3[N:23]=[CH:22][C:21]4=[CH:24][CH:25]=[C:26]([C:27]5[CH:28]=[N:29][N:30]([CH3:32])[CH:31]=5)[N:20]4[N:19]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:7]1

Participants

3

Reactant 2

HCID 115646133-(4-Methylpiperazin-1-yl)anilineHCID 667110872-Methanesulfinyl-7-(1-methyl-1H-pyrazol-4-yl)-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 66711644[3-(4-Methyl-piperazin-1-yl)-phenyl]-[7-(1-methyl-1H-pyrazol-4-yl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amineYield 29.6%

Procedure

3-(4-Methylpiperazin-1-yl)aniline (0.110 g, 0.574 mmol) and 2-Methanesulfinyl-7-(1-methyl-1H-pyrazol-4-yl)-pyrrolo[2,1-f][1,2,4]triazine (0.100 g, 0.383 mmol) were reacted in an analogous manner to Example 881D at 170° C. for 4 hours. Product was purified on Gilson HPLC, lyophilized and free-based with NaHCO3 to afford title compound as a yellow solid (44 mg, 27%) LC/MS: 389 (M+H)HPLC: retention time 1.781 minutes, purity=90%. 1H NMR (400 MHz, DMSO, δ, ppm): 9.65 (br s, 1H), 9.26 (s, 1H), 8.88 (s, 1H), 8.39 (s, 1H), 8.21 (s, 1H), 7.32 (d, J=6.69 Hz, 2H), 7.26 (dd, J=8.61, 8.13 Hz, 1H), 7.04 (d, J=4.8 Hz, 1H), 6.91 (d, J=4.8 Hz, 1H), 6.68 (d, J=7.4 Hz, 1H), 3.94 (s, 3H), 3.78 (d, J=13.0 Hz, 2H), 3.52 (d, J=12.0 Hz, 2H), 3.18-3.16 (m, 2H), 3.00-2.93 (m, 2H), 2.88 (d, J=4.0 Hz, 3H).

Workup

  1. customProduct was purified on Gilson HPLC

Sources & evidence

ORD record
ord-b2d3fd714fd340599ef0ddd13ae05a10
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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