4-(1-Acetylpiperidin-4-yloxy)benzaldehyde → (R)-6-{2-{Ethyl[4-(1-ethylpiperidin-4-yloxy)benzyl]amino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950229Notes

Reaction equation

HRID 1950229 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].[C:31]([N:34]1[CH2:39][CH2:38][CH:37]([O:40][C:41]2[CH:48]=[CH:47][C:44]([CH:45]=O)=[CH:43][CH:42]=2)[CH2:36][CH2:35]1)(=O)[CH3:32]>>[CH2:1]([N:3]([CH2:45][C:44]1[CH:43]=[CH:42][C:41]([O:40][CH:37]2[CH2:38][CH2:39][N:34]([CH2:31][CH3:32])[CH2:35][CH2:36]2)=[CH:48][CH:47]=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 230875244-(1-Acetylpiperidin-4-yloxy)benzaldehydeHCID 57934541pivalic acid (R)-6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 57934261(R)-6-{2-{Ethyl[4-(1-ethylpiperidin-4-yloxy)benzyl]amino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 49.1%

Procedure

Synthesized from pivalic acid (R)-6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (20 mg) and 4-(1-acetylpiperidin-4-yloxy)benzaldehyde (57 mg) according to an analogous synthetic method to Example 264 and purified by LC-MS, the title compound (13 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-c2d2ae12a03e470a9e5af40a02c2c70d
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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