Sodium hydride → 4-(4-(4-Aminophenoxy)-6-cyanoquinolin-7-yloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 388063Notes

Reaction equation

HRID 388063 reaction equation
[NH2:1][C:2]1[CH:21]=[CH:20][C:5]([O:6][C:7]2[C:16]3[C:11](=[CH:12][C:13]([OH:19])=[C:14]([C:17]#[N:18])[CH:15]=3)[N:10]=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[H-].[Na+].[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([CH2:37]CBr)[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:26])[CH3:25]>CN(C)C=O>[C:24]([O:28][C:29]([N:31]1[CH2:36][CH2:35][CH:34]([CH2:37][O:19][C:13]2[CH:12]=[C:11]3[C:16]([C:7]([O:6][C:5]4[CH:20]=[CH:21][C:2]([NH2:1])=[CH:3][CH:4]=4)=[CH:8][CH:9]=[N:10]3)=[CH:15][C:14]=2[C:17]#[N:18])[CH2:33][CH2:32]1)=[O:30])([CH3:27])([CH3:25])[CH3:26]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 10541625tert-Butyl 4-(2-bromoethyl)piperidine-1-carboxylateHCID 1358293904-(4-Aminophenoxy)-6-cyano-7-hydroxyquinoline

Product 1

HCID 672029244-(4-(4-Aminophenoxy)-6-cyanoquinolin-7-yloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After treating 4-(4-aminophenoxy)-7-hydroxyquinoline-6-carbonitrile (0.32 g) with sodium hydride in dimethylformamide in the same manner as Production Example 713-2, it was reacted with 4-bromoethylpiperidine-1-carboxylic acid tert-butyl ester to obtain the title compound (225 mg) as a solid.

Sources & evidence

ORD record
ord-2d940cc0b4704ee1b09090ca27f28832
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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