N,N-Dimethylethylenediamine → HCID 66892998, compound

HRID 1479627Notes

Reaction equation

HRID 1479627 reaction equation
[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:22]=[CH:21][C:17]([C:18](Cl)=[O:19])=[CH:16][C:15]=3[CH3:23])=[CH:7][C:6]=2[C:5]2[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:4]=2[N:3]=1.[CH3:29][N:30]([CH3:34])[CH2:31][CH2:32][NH2:33]>>[NH2:1][C:2]1[C:11]2[N:10]=[CH:9][C:8]([CH2:12][CH2:13][C:14]3[CH:22]=[CH:21][C:17]([C:18]([NH:33][CH2:32][CH2:31][N:30]([CH3:34])[CH3:29])=[O:19])=[CH:16][C:15]=3[CH3:23])=[CH:7][C:6]=2[C:5]2[CH:24]=[CH:25][C:26]([CH3:28])=[CH:27][C:4]=2[N:3]=1

Participants

3

Reactant 2

HCID 66053N,N-DimethylethylenediamineHCID 86652358HCID 86652358, compound

Product 1

HCID 66892998HCID 66892998, compound

Procedure

4-(2-(5-Amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-N-(2-(dimethylamino)ethyl)-3-methylbenzamide was prepared from 4-(2-(5-amino-8-methylbenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylbenzoyl chloride (Example 116/Step 2) and N1,N1-dimethylethane-1,2-diamine following the procedures described for Example 117. 1H NMR (methanol-d4): δ 8.60 (s, 1H), 8.39 (s, 1H), 8.08 (d, 1H), 7.68 (s, 1H), 7.57-7.59 (m, 2H), 7.19-7.22 (m, 2H), 3.57-3.61 (m, 2H), 3.07-3.16 (m, 4H), 2.64-2.67 (m, 2H), 2.52 (s, 3H), 2.38 (s, 6H), 2.35 (s, 3H). LRMS [M+H]=442.3

Sources & evidence

ORD record
ord-86e5f2a724334e56aeef24dfdd335d05
Source dataset
uspto-grants-2016_08
Patent number
US09408907B2

Reaction notes

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