Trifluoroacetic acid → 4-[2-(4-Aminopiperidin-1-yl)ethyl]-6-chloro-1,2,4-benzotriazin-3(4H)-one 1-oxide

HRID 255368Notes

Reaction equation

HRID 255368 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N+:10]([O-:11])=[N:9][C:8](=[O:12])[N:7]([CH2:13][CH2:14][N:15]3[CH2:20][CH2:19][CH:18]([NH:21]C(=O)OC(C)(C)C)[CH2:17][CH2:16]3)[C:6]=2[CH:29]=1.C(O)(C(F)(F)F)=O.NC1CCN(CCN2C3C(=CC(C#N)=CC=3)N=CC2=O)CC1>>[NH2:21][CH:18]1[CH2:17][CH2:16][N:15]([CH2:14][CH2:13][N:7]2[C:6]3[CH:29]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=3[N+:10]([O-:11])=[N:9][C:8]2=[O:12])[CH2:20][CH2:19]1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 667741351-[2-(4-Aminopiperidin-1-yl)ethyl]-2-oxo-1,2-dihydroquinoxaline-6-carbonitrileHCID 86642661tert-Butyl {1-[2-(6-chloro-1-oxido-3-oxo-1,2,4-benzotriazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamate2×

Product 1

HCID 866426604-[2-(4-Aminopiperidin-1-yl)ethyl]-6-chloro-1,2,4-benzotriazin-3(4H)-one 1-oxide

Procedure

tert-Butyl {1-[2-(6-chloro-1-oxido-3-oxo-1,2,4-benzotriazin-4(3H)-yl)ethyl]piperidin-4-yl}carbamate (Intermediate 206, 0.65 g) was deprotected with TFA as described for Intermediate 197 to give the crude free base of the product, 0.517 g.

Workup

  1. customto give the crude free base of the product, 0.517 g

Sources & evidence

ORD record
ord-fd2ad1f92e484c778e5be1d636517023
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

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