(S)-5-(1-Amino-2-(azetidin-1-yl)ethyl)-2-chlorobenzonitrile → (S)-4-((2-(azetidin-1-yl)-1-(4-chloro-3-cyanophenyl)ethyl)amino)benzo[d][1,2,3]triazine-8-carboxamide

HRID 59976Notes

Reaction equation

HRID 59976 reaction equation
[NH2:1][C@@H:2]([C:8]1[CH:9]=[CH:10][C:11]([Cl:16])=[C:12]([CH:15]=1)[C:13]#[N:14])[CH2:3][N:4]1[CH2:7][CH2:6][CH2:5]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:4]1([CH2:3][C@@H:2]([NH:1][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:9]=[CH:10][C:11]([Cl:16])=[C:12]([C:13]#[N:14])[CH:15]=2)[CH2:7][CH2:6][CH2:5]1

Participants

3

Reactant 2

HCID 90190616(S)-5-(1-Amino-2-(azetidin-1-yl)ethyl)-2-chlorobenzonitrileHCID 1785136134-oxo-1H-1,2,3-benzotriazine-8-carboxamide

Product 1

HCID 76072991(S)-4-((2-(azetidin-1-yl)-1-(4-chloro-3-cyanophenyl)ethyl)amino)benzo[d][1,2,3]triazine-8-carboxamide

Procedure

Compound 18 was prepared following general synthetic scheme 7 wherein (S)-5-(1-amino-2-(azetidin-1-yl)ethyl)-2-chlorobenzonitrile was reacted with 4-hydroxybenzo[d][1,2,3]-triazine-8-carboxamide to give the title compound. LC-MS [408 (M+1)], 1H NMR (400 MHz, DMSO-d6): δ 9.31 (s, 1H), 8.82 (d, 1H), 8.63 (d, 1H), 8.55 (d, 1H), 8.12 (d, 1H), 8.03 (t, 2H), 7.85 (dd, 1H), 7.72 (d, 1H), 5.54 (d, 1H), 3.21-3.12 (m, 4H), 3.02-2.97 (m, 1H), 2.83-2.79 (m, 1H).

Workup

  1. customCompound 18 was prepared

Sources & evidence

ORD record
ord-5d86fec40d444c7f907a665841ca1e26
Source dataset
uspto-grants-2016_09
Patent number
US09440968B2

Reaction notes

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