(S)-2-(Azetidin-1-yl)-1-(4-chloro-3-methoxyphenyl)ethanamine → (S)-4-((2-(azetidin-1-yl)-1-(4-chloro-3-methoxyphenyl)ethyl)amino)-benzo[d][1,2,3]triazine-8-carboxamide

HRID 59969Notes

Reaction equation

HRID 59969 reaction equation
[N:1]1([CH2:5][C@H:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[CH:9]=2)[NH2:7])[CH2:4][CH2:3][CH2:2]1.O[C:18]1[C:19]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([NH2:30])=[O:29])[C:20]=2[N:21]=[N:22][N:23]=1>>[N:1]1([CH2:5][C@@H:6]([NH:7][C:18]2[C:19]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([NH2:30])=[O:29])[C:20]=3[N:21]=[N:22][N:23]=2)[C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[CH:9]=2)[CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 90189900(S)-2-(Azetidin-1-yl)-1-(4-chloro-3-methoxyphenyl)ethanamineHCID 1785136134-oxo-1H-1,2,3-benzotriazine-8-carboxamide

Product 1

HCID 76072948(S)-4-((2-(azetidin-1-yl)-1-(4-chloro-3-methoxyphenyl)ethyl)amino)-benzo[d][1,2,3]triazine-8-carboxamide

Procedure

Compound 10 was prepared following general synthetic scheme 7 wherein (S)-2-(azetidin-1-yl)-1-(4-chloro-3-methoxyphenyl)ethanamine was reacted with 4-hydroxybenzo[d][1,2,3]-triazine-8-carboxamide to give the title compound. LC-MS [413 (M+1)], 1H NMR (400 MHz, DMSO-d6): δ 10.01 (s, 1H), 9.29 (s, 1H), 9.08 (d, 1H), 8.58 (d, 2H), 8.08 (t, 2H), 7.44 (d, 2H), 7.15 (dd, 1H), 6.05-6.00 (m, 1H), 4.44-4.41 (m, 1H), 4.26-4.22 (m, 1H), 4.21-4.05 (m, 2H), 3.89 (s, 3H), 3.80-3.74 (m, 3H), 2.49-2.40 (m, 2H).

Workup

  1. customCompound 10 was prepared

Sources & evidence

ORD record
ord-86d1fb245fcf4536af1fa1ead574d024
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Reaction notes

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