Benzonitrile, 3-(bromomethyl)- → 4-{(3-Cyano-benzyl)-[4-(4-methoxycarbonyl-phenoxy)-phenyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1726212Notes

Reaction equation

HRID 1726212 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:27]=[CH:26][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:23]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:32]([C:34]1[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=1)[CH2:37]Br)#[N:33]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH2:37][C:36]2[CH:39]=[CH:40][CH:41]=[C:34]([C:32]#[N:33])[CH:35]=2)[C:15]2[CH:20]=[CH:19][C:18]([O:21][C:22]3[CH:23]=[CH:24][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:27]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 97249Benzonitrile, 3-(bromomethyl)-HCID 68968593HCID 68968593, compound

Product 1

HCID 689717124-{(3-Cyano-benzyl)-[4-(4-methoxycarbonyl-phenoxy)-phenyl]-amino}-piperidine-1-carboxylic acid tert-butyl esterYield 90%

Procedure

Using general procedure H, 4-[4-(4-methoxycarbonyl-phenoxy)-phenylamino]-piperidine-1-carboxylic acid tert-butyl ester (see EXAMPLE 96) (440 mg, 1.07 mmol) and 3-cyanobenzyl bromide (314 mg, 1.6 mmol) afforded 4-{(3-cyano-benzyl)-[4-(4-methoxycarbonyl-phenoxy)-phenyl]-amino}-piperidine-1-carboxylic acid tert-butyl ester as a white solid (520 mg, 90%).

Sources & evidence

ORD record
ord-e122e4dc61a54937a85291b3f53e3eb2
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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