1,2-Ethanediamine, N1,N1,N2-trimethyl- → 4-(3,5-Dichloropyridin-4-ylamino)-8-(5-((2-(dimethylamino)ethyl)(methyl)amino)pentyloxy)-7-methoxy-2H-chromen-2-one

HRID 20712

Reaction equation

HRID 20712 reaction equation
[CH3:1][N:2]([CH3:7])[CH2:3][CH2:4][NH:5][CH3:6].Br[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[C:16]([O:35][CH3:36])=[CH:17][CH:18]=[C:19]2[C:24]=1[O:23][C:22](=[O:25])[CH:21]=[C:20]2[NH:26][C:27]1[C:32]([Cl:33])=[CH:31][N:30]=[CH:29][C:28]=1[Cl:34]>>[Cl:34][C:28]1[CH:29]=[N:30][CH:31]=[C:32]([Cl:33])[C:27]=1[NH:26][C:20]1[C:19]2[C:24](=[C:15]([O:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][N:5]([CH2:4][CH2:3][N:2]([CH3:7])[CH3:1])[CH3:6])[C:16]([O:35][CH3:36])=[CH:17][CH:18]=2)[O:23][C:22](=[O:25])[CH:21]=1

Participants

3

Reactant 2

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 248495698-(5-Bromopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one

Product 1

HCID 248493414-(3,5-Dichloropyridin-4-ylamino)-8-(5-((2-(dimethylamino)ethyl)(methyl)amino)pentyloxy)-7-methoxy-2H-chromen-2-one

Procedure

The title compound was prepared from N1,N1,N2-trimethylethane-1,2-diamine and 8-(5-bromopentyloxy)-4-(3,5-dichloropyridin-4-ylamino)-7-methoxy-2H-chromen-2-one (Example 28) following the procedure outlined in Example 52. 1H NMR (400 MHz, DMSO-d6): δ 8.57 (s, 2H), 7.85 (d, 1H), 7.05 (d, 1H), 4.23 (br s, 1H), 3.96 (t, 2H), 3.87 (s, 3H), 2.65 (m, 4H), 2.55 (m, 2H), 2.34 (s, 6H), 2.31 (s, 3H), 1.69 (m, 2H), 1.51 (m, 4H); MS (ESI): 523.0.

Sources & evidence

ORD record
ord-531d9de4d8c049379ca3c8fd95ea8cb5
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Linked notes

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