2-Bromo-1-(3,3-dimethylpiperidin-1-yl)ethanone → 6-{2-{{4-[2-(3,3-Dimethylpiperidin-1-yl)ethoxy]-3-fluorobenzyl}methylamino}-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950436Notes

Reaction equation

HRID 1950436 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][C:36]=1[OH:37])[C:5]([CH2:7][NH:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[CH:17]1[CH2:26][CH2:25][C:24]2[CH:23]=[C:22]([O:27]C(=O)C(C)(C)C)[CH:21]=[CH:20][C:19]=2[CH2:18]1)=O.Br[CH2:39][C:40]([N:42]1[CH2:47][CH2:46][CH2:45][C:44]([CH3:49])([CH3:48])[CH2:43]1)=O>>[CH3:48][C:44]1([CH3:49])[CH2:45][CH2:46][CH2:47][N:42]([CH2:40][CH2:39][O:37][C:36]2[CH:35]=[CH:34][C:4]([CH2:5][CH2:7][NH:8][C:9]3[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=3[CH:17]3[CH2:26][CH2:25][C:24]4[CH:23]=[C:22]([OH:27])[CH:21]=[CH:20][C:19]=4[CH2:18]3)=[CH:3][C:2]=2[F:1])[CH2:43]1

Participants

3

Reactant 2

HCID 233637862-Bromo-1-(3,3-dimethylpiperidin-1-yl)ethanoneHCID 66626888Pivalic acid 6-{2-[(3-fluoro-4-hydroxybenzoyl)methylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 666259196-{2-{{4-[2-(3,3-Dimethylpiperidin-1-yl)ethoxy]-3-fluorobenzyl}methylamino}-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-olYield 50.9%

Procedure

Synthesized from pivalic acid 6-{2-[(3-fluoro-4-hydroxybenzoyl)methylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (20 mg) and 2-bromo-1-(3,3-dimethylpiperidin-1-yl)ethanone (19 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (11 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-8b3b94be591b416da90f7ac1adcd7149
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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