Potassium Carbonate → 3-Amino-5-({7-chloro-1-[2-(piperidin-1-yl) ethyl]-1,4-dihydroquinolin-4 ylidene}amino)benzonitrile

HRID 1190900Notes

Reaction equation

HRID 1190900 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+].CCN(C(C)C)C(C)C>C(#N)C>[NH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([N: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:10]=1)[C:6]#[N:7]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 74826Piperidine, 1-(2-chloroethyl)-, hydrochlorideHCID 81531DiisopropylethylamineHCID 672483483-Amino-5-[(7-chloroquinolin-4-yl)amino]benzonitrile hydrochloride

Product 1

HCID 672472943-Amino-5-({7-chloro-1-[2-(piperidin-1-yl) ethyl]-1,4-dihydroquinolin-4 ylidene}amino)benzonitrileYield 3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-Amino-5-[(7-chloroquinolin-4-yl)amino]benzonitrile hydrochloride prepared from step B of example 19 (200 mg, 0.68 mmol), 1-(2-chloroethyl)piperidine hydrochloride (125 mg, 1 eq), K2CO3 (468 mg, 5 eq) and DIEA (0.11 mL, 1 eq) were refluxed in 30 mL of acetonitrile for 72 h. The reaction mixture was then filtered. The filtrate was evaporated and the residue was purified by flash chromatography on silica gel (AcOEt/MeOH//100/0 to 95/5) to yield expected compound as a yellow powder (8 mg, 3% yield). m/z (ESI) 406.2 [M+H]+.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. customThe filtrate was evaporated
  3. customthe residue was purified by flash chromatography on silica gel (AcOEt/MeOH//100/0 to 95/5)

Sources & evidence

ORD record
ord-b2f4bee1a67a4488aee1c4bfaacaeb25
Source dataset
uspto-grants-2014_03
Patent number
US08680095B2

Reaction notes

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