1,5-Dibromopentane → 4-(3-Chloro-4-(pyridin-2-YL-methoxy)phenylamino)-6-(piperidin-1-YL)-7-(tetrahydrofuran-3-YL-oxy)quinoline-3-carbonitrile

HRID 714588Notes

Reaction equation

HRID 714588 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12][CH:13]1[CH2:17][CH2:16][O:15][CH2:14]1)[N:8]=[CH:7][C:6]([C:18]#[N:19])=[C:5]2[NH:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=2)=[C:23]([Cl:35])[CH:22]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47]Br>C(Cl)(Cl)Cl>[Cl:35][C:23]1[CH:22]=[C:21]([NH:20][C:5]2[C:4]3[C:9](=[CH:10][C:11]([O:12][CH:13]4[CH2:17][CH2:16][O:15][CH2:14]4)=[C:2]([N:1]4[CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]4)[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:18]#[N:19])[CH:26]=[CH:25][C:24]=1[O:27][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=1

Participants

5

Reactant 3

HCID 81001,5-DibromopentaneHCID 11430Potassium CarbonateHCID 866945566-Amino-4-(3-chloro-4-(pyridin-2-yl-methoxy)phenylamino)-7-(tetrahydrofuran-3-yl-oxy)quinolin-3-carbonitrile

Product 1

HCID 866945574-(3-Chloro-4-(pyridin-2-YL-methoxy)phenylamino)-6-(piperidin-1-YL)-7-(tetrahydrofuran-3-YL-oxy)quinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a single-neck reaction flask (50 ml) were added 6-amino-4-(3-chloro-4-(pyridin-2-yl-methoxy)phenylamino)-7-(tetrahydrofuran-3-yl-oxy)quinolin-3-carbonitrile (20 mg, 0.041 mmol), anhydrous potassium carbonate powder (10 mg) and chloroform (5 ml). To the flask was added 1,5-dibromopentane (10 mg). The mixture was stirred at the room temperature. After the reaction finished, the mixture was filtered. The filtrate was rotary-evaporated to dryness. The residue was purified with thin layer chromatography (developing solvent: chloroform:methanol=9:1) to give a pure product.

Workup

  1. filtrationthe mixture was filtered
  2. customThe filtrate was rotary-evaporated to dryness
  3. customThe residue was purified with thin layer chromatography (developing solvent: chloroform:methanol=9:1)
  4. customto give a pure product

Sources & evidence

ORD record
ord-0360edb677f349b2ad6195c5c561118d
Source dataset
uspto-grants-2015_11
Patent number
US09187458B2

Reaction notes

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