tert-Butyl 4-(bromomethyl)piperidine-1-carboxylate → Tert-butyl 4-(((4-(3-chloro-4-((cyclopropylamino)carbonyl)aminophenoxy)-6-cyano-7-quinolyl)oxy)methyl)-1-piperidinecarboxylate

HRID 387900Notes

Reaction equation

HRID 387900 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[OH:13])[N:9]=[CH:8][CH:7]=[C:6]2[O:14][C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22]([NH:24][CH:25]2[CH2:27][CH2:26]2)=[O:23])=[C:17]([Cl:28])[CH:16]=1)#[N:2].Br[CH2:30][CH:31]1[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:33][CH2:32]1>>[Cl:28][C:17]1[CH:16]=[C:15]([CH:20]=[CH:19][C:18]=1[NH:21][C:22]([NH:24][CH:25]1[CH2:26][CH2:27]1)=[O:23])[O:14][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH2:30][CH:31]3[CH2:36][CH2:35][N:34]([C:37]([O:39][C:40]([CH3:41])([CH3:43])[CH3:42])=[O:38])[CH2:33][CH2:32]3)=[C:3]([C:1]#[N:2])[CH:4]=2)[N:9]=[CH:8][CH:7]=1

Participants

3

Reactant 2

HCID 15512811tert-Butyl 4-(bromomethyl)piperidine-1-carboxylateHCID 135829385n-(4-(6-Cyano-7-hydroxy-4-quinolyl)oxy-2-chlorophenyl)-n'-cyclopropylurea

Product 1

HCID 22936576Tert-butyl 4-(((4-(3-chloro-4-((cyclopropylamino)carbonyl)aminophenoxy)-6-cyano-7-quinolyl)oxy)methyl)-1-piperidinecarboxylateYield 14.6%

Procedure

The title compound (275.8 mg, 0.466 mmol, 14.6%) was obtained as white crystals from an N-(4-(6-cyano-7-hydroxy-4-quinolyl)oxy-2-chlorophenyl)-N′-cyclopropylurea crude product (1.00 g, 3.20 mmol) and tert-butyl 4-(bromomethyl)-1-piperidinecarboxylate, by the same procedure as in Example 7.

Sources & evidence

ORD record
ord-ae196dd7f2ee4da080cc180dea531da8
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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