(S)-1-(4-chloro-3-methoxyphenyl)-N2,N2-dimethylethane-1,2-diamine → (S)-4-((1-(4-chloro-3-methoxyphenyl)-2-(dimethylamino)ethyl)amino)-benzo[d][1,2,3]triazine-8-carboxamide

HRID 59970Notes

Reaction equation

HRID 59970 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH2:13])[CH2:9][N:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[O:14][CH3:15].O[C:17]1[C:18]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([NH2:29])=[O:28])[C:19]=2[N:20]=[N:21][N:22]=1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:13][C:17]2[C:18]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([NH2:29])=[O:28])[C:19]=3[N:20]=[N:21][N:22]=2)[CH2:9][N:10]([CH3:12])[CH3:11])=[CH:4][C:3]=1[O:14][CH3:15]

Participants

3

Reactant 2

HCID 90190098(S)-1-(4-chloro-3-methoxyphenyl)-N2,N2-dimethylethane-1,2-diamineHCID 1785136134-oxo-1H-1,2,3-benzotriazine-8-carboxamide

Product 1

HCID 76072949(S)-4-((1-(4-chloro-3-methoxyphenyl)-2-(dimethylamino)ethyl)amino)-benzo[d][1,2,3]triazine-8-carboxamide

Procedure

Compound 11 was prepared following general synthetic scheme 7 wherein (S)-1-(4-chloro-3-methoxyphenyl)-N2,N2-dimethylethane-1,2-diamine was reacted with 4-hydroxybenzo[d][1,2,3]-triazine-8-carboxamide to give the title compound. LC-MS [401 (M+1)], 1H NMR (400 MHz, DMSO-d6): δ 9.51 (s, 1H), 9.27 (s, 1H), 9.09 (d, 1H), 8.58 (dd, 2H), 8.08 (t, 2H), 7.44 (d, 2H), 7.18 (dd, 1H), 6.26 (t, 1H), 3.89 (s, 3H), 3.83-3.76 (m, 1H), 3.62-3.57 (m, 1H), 2.92 (d, 6H).

Workup

  1. customCompound 11 was prepared

Sources & evidence

ORD record
ord-cac3e4fd03e44cf698400d0d383ffc99
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Reaction notes

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