3-[(4-Methylpiperazin-1-yl)methyl]aniline → N-[3-(4-methylpiperazin-1-ylmethyl)phenyl]-2-chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)benzamide

HRID 1007136Notes

Reaction equation

HRID 1007136 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=2)[NH2:12])[CH2:4][CH2:3]1.[Cl:16][C:17]1[CH:25]=[CH:24][C:23]([NH:26][C:27]([C:29]2[CH:34]=[CH:33][N:32]=[C:31]([N:35]3[CH2:40][CH2:39][O:38][CH2:37][CH2:36]3)[CH:30]=2)=[O:28])=[CH:22][C:18]=1[C:19](O)=[O:20]>>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][C:9]2[CH:10]=[C:11]([NH:12][C:19](=[O:20])[C:18]3[CH:22]=[C:23]([NH:26][C:27]([C:29]4[CH:34]=[CH:33][N:32]=[C:31]([N:35]5[CH2:36][CH2:37][O:38][CH2:39][CH2:40]5)[CH:30]=4)=[O:28])[CH:24]=[CH:25][C:17]=3[Cl:16])[CH:13]=[CH:14][CH:15]=2)[CH2:4][CH2:3]1

Participants

3

Reactant 2

HCID 64841863-[(4-Methylpiperazin-1-yl)methyl]anilineHCID 226677762-Chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)benzoic acid

Product 1

HCID 9850509N-[3-(4-methylpiperazin-1-ylmethyl)phenyl]-2-chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)benzamideYield 32%

Procedure

Using an analogous procedure to that described in Example 4, 3-(4-methylpiperazin-1-ylmethyl)aniline was reacted with 2-chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)benzoic acid to give the title compound in 32% yield; NMR Spectrum: (DMSOd6) 2.13 (s, 3H), 2.31-2.35 (m, 8H), 3.42 (s, 2H), 3.49-3.53 (m, 4H), 3.69-3.72 (m, 4H), 7.02 (d, 1H), 7.1 (d, 1H), 7.22-7.3 (m, 2H), 7.57-7.65 (m, 3H), 7.84-7.94 (m, 2H), 8.28 (d, 1H), 10.47 (s, 1H), 10.52 (s, 1H); Mass Spectrum: M+H+ 549 and 551.

Sources & evidence

ORD record
ord-1c00e68caf8148289d8d3119fe1a5d3c
Source dataset
uspto-grants-2004_09
Patent number
US06794380B2

Reaction notes

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