Dimethylamine → 4-(3,5-dichloropyridin-4-ylamino)-8-(6-(dimethylamino)hexyloxy)-7-methoxy-2H-chromen-2-one

HRID 20695

Reaction equation

HRID 20695 reaction equation
[CH3:1][NH:2][CH3:3].Br[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]Br.[Cl:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Cl:34])[C:18]=1[NH:19][C:20]1[C:29]2[C:24](=[C:25]([OH:32])[C:26]([O:30][CH3:31])=[CH:27][CH:28]=2)[O:23][C:22](=[O:33])[CH:21]=1>>[Cl:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17]([Cl:34])[C:18]=1[NH:19][C:20]1[C:29]2[C:24](=[C:25]([O:32][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][N:2]([CH3:3])[CH3:1])[C:26]([O:30][CH3:31])=[CH:27][CH:28]=2)[O:23][C:22](=[O:33])[CH:21]=1

Participants

4

Reactant 3

HCID 674DimethylamineHCID 123681,6-DibromohexaneHCID 248495704-(3,5-dichloropyridin-4-ylamino)-8-hydroxy-7-methoxy-2H-chromen-2-one

Product 1

HCID 248492554-(3,5-dichloropyridin-4-ylamino)-8-(6-(dimethylamino)hexyloxy)-7-methoxy-2H-chromen-2-one

Procedure

The title compound was prepared from dimethylamine, 1,6-dibromohexane, and 4-(3,5-dichloropyridin-4-ylamino)-8-hydroxy-7-methoxy-2H-chromen-2-one (Example 29) following the procedures outlined in Examples 25 & 27. 1H NMR (400 MHz, DMSO-d6): δ 9.38 (br s, 1H), 8.57 (s, 2H), 7.85 (d, 1H), 7.05 (d, 1H), 4.24 (br s, 1H), 3.96 (t, 2H), 3.87 (s, 3H), 2.55 (br, 2H), 2.37 (s, 6H), 1.67 (m, 2H), 1.49 (m, 4H), 1.34 (m, 2H); MS (ESI): 479.9.

Sources & evidence

ORD record
ord-1facfed5f0794cea8bcd6e434d1de8e3
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Linked notes

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