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

HRID 1950221Notes

Reaction equation

HRID 1950221 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].[N:31]1([CH2:38][CH2:39][C:40]2[S:44][C:43]([C:45]([O-])=O)=[CH:42][CH:41]=2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.[Li+]>>[N:31]1([CH2:38][CH2:39][C:40]2[S:44][C:43]([CH2:45][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:42][CH:41]=2)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

3

Reactant 2

HCID 57934541pivalic acid (R)-6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl esterHCID 66627078Lithium 5-(2-azepan-1-ylethyl)thiophene-2-carboxylate

Product 1

HCID 57934481(R)-6-{2-{[5-(2-Azepan-1-ylethyl)thiophen-2-ylmethyl]ethylamino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 97.5%

Procedure

Synthesized from pivalic acid (R)-6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (30 mg) and lithium 5-(2-azepan-1-ylethyl)thiophene-2-carboxylate (60 mg) according to an analogous synthetic method to Example 152 and purified by LC-MS, the title compound (39 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-32c34c81ba9447a9acaefdaa65dcb065
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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