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

HRID 1950218Notes

Reaction equation

HRID 1950218 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[CH: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][O:40][C:41]2[CH:42]=[CH:43][C:44]([C:47]([O-])=O)=[N:45][CH:46]=2)[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1.[Na+]>>[N:31]1([CH2:38][CH2:39][O:40][C:41]2[CH:42]=[CH:43][C:44]([CH2:47][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[CH: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)=[N:45][CH:46]=2)[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

3

Reactant 2

HCID 57933854Pivalic acid 6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl esterHCID 66626726Sodium 5-(2-azepan-1-ylethoxy)pyridine-2-carboxylate

Product 1

HCID 579345036-{2-{[5-(2-Azepan-1-ylethoxy)pyridin-2-ylmethyl]ethylamino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 47.1%

Procedure

Synthesized from pivalic acid 6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (25 mg) and sodium 5-(2-azepan-1-ylethoxy)pyridine-2-carboxylate (60 mg) according to an analogous synthetic method to Example 152, the title compound (16 mg) was obtained.

Sources & evidence

ORD record
ord-b1497b09da434923a76bd02be24709d9
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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