4-Dimethylaminobutylamine → N-[2-chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)phenyl]-6-(4-dimethylaminobutylamino)pyridine-3-carboxamide

HRID 1828739Notes

Reaction equation

HRID 1828739 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][CH2:38][NH2:39]>>[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]([NH:39][CH2:38][CH2:37][CH2:36][CH2:35][N:34]([CH3:40])[CH3:33])=[CH:3][CH:4]=1)=[O:9]

Participants

3

Reactant 2

HCID 770634-DimethylaminobutylamineHCID 220579436-chloro-N-[2-chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)phenyl]pyridine-3-carboxamide

Product 1

HCID 22057988N-[2-chloro-5-(2-morpholinopyrid-4-ylcarbonylamino)phenyl]-6-(4-dimethylaminobutylamino)pyridine-3-carboxamideYield 61%

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 4-dimethylaminobutylamine to give the title compound in 61% yield; NMR Spectrum: (DMSOd6) 1.49 (m, 4H), 2.09 (s, 6H), 2.19 (t, 2H), 3.51 (m, 4H), 3.71 (m, 4H), 6.49 (d, 1H), 7.1 (d, 1H), 7.23 (m, 2H), 7.5 (d, 1H), 7.68 (d, 1H), 7.89 (d, 1H), 8.06 (s, 1H), 8.27 (d, 1H), 8.64 (s, 1H), 9.64 (s, 1H), 10.44 (s, 1H); Mass Spectrum: M+H+ 552 and 554.

Sources & evidence

ORD record
ord-2f13c4bdb4cd46f99a8e018d265dea81
Source dataset
uspto-grants-2006_06
Patent number
US07060700B2

Reaction notes

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