Potassium Carbonate → 4-[(3-Amino-5-cyanophenyl)amino]-7-chloro-1-[2-(piperidin-1-yl)ethyl]quinolin-1-ium chloride

HRID 1190899Notes

Reaction equation

HRID 1190899 reaction equation
Cl.[NH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([Cl:22])=[CH:19][CH:20]=3)[N:15]=[CH:14][CH:13]=2)[CH:10]=1)[C:6]#[N:7].Cl.Cl[CH2:25][CH2:26][N:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[Cl-:22].[NH2:2][C:3]1[CH:10]=[C:9]([NH:11][C:12]2[C:21]3[C:16](=[CH:17][C:18]([Cl:22])=[CH:19][CH:20]=3)[N+:15]([CH2:25][CH2:26][N:27]3[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]3)=[CH:14][CH:13]=2)[CH:8]=[C:5]([C:6]#[N:7])[CH:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 672483483-Amino-5-[(7-chloroquinolin-4-yl)amino]benzonitrile hydrochloride

Product 1

HCID 672468024-[(3-Amino-5-cyanophenyl)amino]-7-chloro-1-[2-(piperidin-1-yl)ethyl]quinolin-1-ium chlorideYield 88%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Amino-5-[(7-chloroquinolin-4-yl)amino]benzonitrile hydrochloride prepared from step B of example 19 (0.88 g, 2.98 mmol), 1-(2-chloroethyl)piperidine hydrochloride (0.55 g, 1 eq) and K2CO3 (0.83 g, 2 eq) were refluxed in 50 mL of acetonitrile for 48 h. The reaction mixture was then filtered. The filtrate was evaporated to yield expected compound as a yellow powder (0.58 g, 44% yield). m/z (ESI) 406.2 [M]+.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-3b34b32088094f679fadafc492c7f071
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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