Hydrochloric Acid → 3-[(7-Chloroquinolin-4-yl)amino]-5-{[2-(piperidin-1-yl)ethyl]amino}benzonitrile

HRID 1190903Notes

Reaction equation

HRID 1190903 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([NH:10][CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH:9]=1)[C:5]#[N:6].Cl[C:20]1[C:29]2[C:24](=[CH:25][C:26]([Cl:30])=[CH:27][CH:28]=2)[N:23]=[CH:22][CH:21]=1.Cl>C(O)C>[Cl:30][C:26]1[CH:25]=[C:24]2[C:29]([C:20]([NH:1][C:2]3[CH:3]=[C:4]([CH:7]=[C:8]([NH:10][CH2:11][CH2:12][N:13]4[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]4)[CH:9]=3)[C:5]#[N:6])=[CH:21][CH:22]=[N:23]2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 68664,7-DichloroquinolineHCID 672465403-Amino-5-{[2-(piperidin-1-yl)ethyl]amino}benzonitrile

Product 1

HCID 672469973-[(7-Chloroquinolin-4-yl)amino]-5-{[2-(piperidin-1-yl)ethyl]amino}benzonitrileYield 15.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-amino-5-{[2-(piperidin-1-yl)ethyl]amino}benzonitrile (200 mg, 0.82 mmol) and 4,7-dichloroquinoline (162 mg, 1 eq) were refluxed in 15 mL of ethanol and 0.82 mL of HCl 1M for 24 h. The reaction mixture was then evaporated and the residue and was purified by preparative thin-layer chromatography (DCM/MeOH/NH4OH//95/5/1) to yield expected compound as a yellow powder (51 mg, 15% yield). m/z (ESI) 406.3 [M+H]+.

Workup

  1. customThe reaction mixture was then evaporated
  2. customthe residue and was purified by preparative thin-layer chromatography (DCM/MeOH/NH4OH//95/5/1)

Sources & evidence

ORD record
ord-3fc70af493b84577a0e8a8f430104655
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

Loading…