pivalic acid (R)-6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester → (R)-6-{2-{[6-(2-Azepan-1-ylethoxy)pyridin-3-ylmethyl]ethylamino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950222Notes

Reaction equation

HRID 1950222 reaction equation
[CH2:1]([NH:3][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.[N:32]1([CH2:39][CH2:40][O:41][C:42]2[CH:50]=[CH:49][C:45]([C:46](O)=O)=[CH:44][N:43]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1>>[N:32]1([CH2:39][CH2:40][O:41][C:42]2[N:43]=[CH:44][C:45]([CH2:46][N:3]([CH2:1][CH3:2])[C:4]3[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=3[C@@H:14]3[CH2:23][CH2:22][C:21]4[CH:20]=[C:19]([OH:24])[CH:18]=[CH:17][C:16]=4[CH2:15]3)=[CH:49][CH:50]=2)[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]1

Participants

3

Reactant 2

HCID 57934541pivalic acid (R)-6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl esterHCID 666267216-(2-Azepan-1-ylethoxy)nicotinic acid hydrochloride

Product 1

HCID 57933903(R)-6-{2-{[6-(2-Azepan-1-ylethoxy)pyridin-3-ylmethyl]ethylamino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 63.7%

Procedure

Synthesized from pivalic acid (R)-6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (30 mg) and 6-(2-azepan-1-ylethoxy)nicotinic acid hydrochloride (60 mg) according to an analogous synthetic method to Example 337 described below and purified by LC-MS, the title compound (26 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-799ebac4bb024929af50b02c96abaf9a
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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