1,3-Propanediamine, N1,N1,N3-trimethyl- → N-[2-chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)phenyl]-6-[N-(3-dimethylaminopropyl)-N-methylamino]pyridine-3-carboxamide

HRID 2302264Notes

Reaction equation

HRID 2302264 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]([NH:10][C:11]2[CH:16]=[C:15]([NH:17][C:18]([C:20]3[CH:25]=[CH:24][N:23]=[C:22]([N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[CH:21]=3)=[O:19])[CH:14]=[CH:13][C:12]=2[Cl:32])=[O:9])=[CH:4][CH:3]=1.[CH3:33][N:34]([CH3:40])[CH2:35][CH2:36][CH2:37][NH:38][CH3:39]>>[Cl:32][C:12]1[CH:13]=[CH:14][C:15]([NH:17][C:18]([C:20]2[CH:25]=[CH:24][N:23]=[C:22]([N:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[CH:21]=2)=[O:19])=[CH:16][C:11]=1[NH:10][C:8]([C:5]1[CH:6]=[N:7][C:2]([N:38]([CH2:37][CH2:36][CH2:35][N:34]([CH3:40])[CH3:33])[CH3:39])=[CH:3][CH:4]=1)=[O:9]

Participants

3

Reactant 2

HCID 783021,3-Propanediamine, N1,N1,N3-trimethyl-HCID 220579436-chloro-N-[2-chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)phenyl]pyridine-3-carboxamide

Product 1

HCID 22058007N-[2-chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)phenyl]-6-[N-(3-dimethylaminopropyl)-N-methylamino]pyridine-3-carboxamideYield 73%

Procedure

Using an analogous procedure to that described in Example 21, 6-chloro-N-[2-chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)phenyl]pyridine-3-carboxamide was reacted with N-(3-dimethylaminopropyl)-N-methylamine to give the title compound in 73% yield; NMR Spectrum: (DMSOd6) 1.67 (m, 2H), 2.12 (s, 6H), 2.21 (t, 2H), 3.07 (s, 3H), 3.51 (m, 4H), 3.58 (m, 2H), 3.71 (m, 4H), 6.69 (d, 1H), 7.1 (d, 1H), 7.23 (s, 1H), 7.5 (d, 1H), 8.04 (m, 2H), 8.28 (d, 1H), 8.72 (s, 1H), 9.7 (s, 1H), 10.44 (s, 1H); Mass Spectrum: M+H+ 552 and 554.

Sources & evidence

ORD record
ord-493acaf1a686472fa18356b76cba6280
Source dataset
uspto-grants-2002_08
Patent number
US06432949B1

Reaction notes

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