2-(Methylamino)ethanol → 4-(3,5-Dimethylpyridin-4-ylamino)-8-(6-((2-hydroxyethyl)(methyl)amino)hexyloxy)-7-methoxyquinolin-2(1H)-one

HRID 1095819Notes

Reaction equation

HRID 1095819 reaction equation
Cl[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][C:9]1[C:10]([O:29][CH3:30])=[CH:11][CH:12]=[C:13]2[C:18]=1[NH:17][C:16](=[O:19])[CH:15]=[C:14]2[NH:20][C:21]1[C:26]([CH3:27])=[CH:25][N:24]=[CH:23][C:22]=1[CH3:28].[CH3:31][NH:32][CH2:33][CH2:34][OH:35]>>[CH3:28][C:22]1[CH:23]=[N:24][CH:25]=[C:26]([CH3:27])[C:21]=1[NH:20][C:14]1[C:13]2[C:18](=[C:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][N:32]([CH2:33][CH2:34][OH:35])[CH3:31])[C:10]([O:29][CH3:30])=[CH:11][CH:12]=2)[NH:17][C:16](=[O:19])[CH:15]=1

Participants

3

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 592681148-(6-chlorohexyloxy)-4-(3,5-dimethylpyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one2×

Product 1

HCID 533448384-(3,5-Dimethylpyridin-4-ylamino)-8-(6-((2-hydroxyethyl)(methyl)amino)hexyloxy)-7-methoxyquinolin-2(1H)-one

Procedure

The title compound was prepared from 8-(6-chlorohexyloxy)-4-(3,5-dimethylpyridin-4-ylamino)-7-methoxyquinolin-2(1H)-one (Intermediate 6) and and 2-(methylamino)ethanol following the procedure outlined in Example 18, Step 2 (modifications: 22° C., 60 h). 1H NMR (300 MHz, DMSO-d6):):δ: 9.67 (s, 1H), 8.42 (s, 3H), 7.91 (d, J=9 Hz, 1H), 7.04 (s, J=7 Hz, 1H), 4.55 (s, 1H), 4.31 (s, 1H), 3.98 (t, J=6.6 Hz, 5H), 3.46 (s, 2H), 2.40-2.28 (m, 4H), 2.15 (s, 9H), 1.75 (m, 2H), 1.35 (m, 6H). MS (ESI) 469.

Workup

  1. customoutlined in Example 18, Step 2 (modifications: 22° C., 60 h)

Sources & evidence

ORD record
ord-506cf4616f5141ab88e7ad15e3ec55a1
Source dataset
uspto-grants-2012_03
Patent number
US08138205B2

Reaction notes

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