2-Chloro-1-piperidine-1-yl-ethanone → (R)-6-{2-{Ethyl[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl]amino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950552Notes

Reaction equation

HRID 1950552 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].Cl[CH2:42][C:43]([N:45]1[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1)=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[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]2)=[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[CH2:15][CH2:16][C:21]2[CH:20]=[C:19]([OH:24])[CH:18]=[CH:17][C:22]=2[CH2:23]1)[CH3:2]

Participants

3

Reactant 2

HCID 2223122-Chloro-1-piperidine-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 58023105(R)-6-{2-{Ethyl[3-fluoro-4-(2-piperidin-1-ylethoxy)benzyl]amino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 24.7%

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-chloro-1-piperidin-1-ylethanone (8.8 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (3.8 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-6cb0c80acfe740b2b7a88129a6089de7
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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