2-Bromo-1-(2,2,6,6-tetramethylpiperidin-1-yl)ethanone → (R)-6-{2-{Ethyl{3-fluoro-4-[2-(2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]benzyl}amino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950554Notes

Reaction equation

HRID 1950554 reaction equation
[CH2:1]([N:3]([C:31](=O)[C:32]1[CH:37]=[CH:36][C:35]([OH:38])=[C:34]([F:39])[CH:33]=1)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[C@@H:14]1[CH2:23][CH2:22][C:21]2[CH:20]=[C:19]([O:24]C(=O)C(C)(C)C)[CH:18]=[CH:17][C:16]=2[CH2:15]1)[CH3:2].Br[CH2:42][C:43]([N:45]1[C:50]([CH3:52])([CH3:51])[CH2:49][CH2:48][CH2:47][C:46]1([CH3:54])[CH3:53])=O>>[CH2:1]([N:3]([CH2:31][C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:42][CH2:43][N:45]2[C:50]([CH3:52])([CH3:51])[CH2:49][CH2:48][CH2:47][C:46]2([CH3:54])[CH3:53])=[C:34]([F:39])[CH:33]=1)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=1[C@@H:14]1[CH2:23][CH2:22][C:21]2[CH:20]=[C:19]([OH:24])[CH:18]=[CH:17][C:16]=2[CH2:15]1)[CH3:2]

Participants

3

Reactant 2

HCID 230874492-Bromo-1-(2,2,6,6-tetramethylpiperidin-1-yl)ethanoneHCID 57934194Pivalic acid (R)-6-{2-[ethyl(3-fluoro-4-hydroxybenzoyl)amino]-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 57934363(R)-6-{2-{Ethyl{3-fluoro-4-[2-(2,2,6,6-tetramethylpiperidin-1-yl)ethoxy]benzyl}amino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 23.1%

Procedure

Synthesized from pivalic acid (R)-6-{2-[ethyl(3-fluoro-4-hydroxybenzoyl)amino]-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (15 mg) and 2-bromo-1-(2,2,6,6-tetramethylpiperidin-1-yl)ethanone (14 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (3.9 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-89c73a0474334abfb42ea2951180ca3f
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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