1,2-Ethanediamine, N1,N1,N2-trimethyl- → HCID 58213508, compound

HRID 340347Notes

Reaction equation

HRID 340347 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][CH:26]=[CH:27][C:4]=2[N:3]=1.[CH3:28][N:29]([CH3:34])[CH2:30][CH2:31][NH:32][CH3:33]>>[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]([N:32]([CH2:31][CH2:30][N:29]([CH3:34])[CH3:28])[CH3:33])=[O:19])=[CH:16][C:15]=3[CH3:23])=[CH:7][C:6]=2[C:5]2[CH:24]=[CH:25][CH:26]=[CH:27][C:4]=2[N:3]=1

Participants

3

Reactant 2

HCID 673381,2-Ethanediamine, N1,N1,N2-trimethyl-HCID 86652359HCID 86652359, compound

Product 1

HCID 58213508HCID 58213508, compound

Procedure

4-(2-(5-Aminobenzo[f][1,7]naphthyridin-2-yl)ethyl)-N-(2-(dimethylamino)ethyl)-N,3-dimethylbenzamide was prepared from 4-(2-(5-aminobenzo[f][1,7]naphthyridin-2-yl)ethyl)-3-methylbenzoyl chloride (Example 116/Step 2) and N1,N1,N2-trimethylethane-1,2-diamine following the procedures described for Example 117. 1H NMR (methanol-d4): δ 8.84 (s, 1H), 8.63 (s, 1H), 8.39 (d, 1H), 7.76-7.83 (m, 2H), 7.60-7.64 (m, 1H), 7.37 (s, 1H), 7.19-7.29 (m, 2H), 3.96 (t, 2H), 3.48 (t, 2H), 3.32 (t, 2H), 3.20 (t, 2H), 3.09 (s, 3H), 3.06 (s, 6H), 2.42 (s, 3H). LRMS [M+H]=442.3

Sources & evidence

ORD record
ord-9c9ac77cb5a14052878b32266520c806
Source dataset
uspto-grants-2014_11
Patent number
US08895577B2

Reaction notes

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