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

HRID 1950204Notes

Reaction equation

HRID 1950204 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[C@@H:12]1[CH2:21][CH2:20][C:19]2[CH:18]=[C:17]([O:22]C(=O)C(C)(C)C)[CH:16]=[CH:15][C:14]=2[CH2:13]1)[CH3:2].[C:29]([N:32]1[CH2:37][CH2:36][CH:35]([O:38][C:39]2[CH:46]=[CH:45][C:42]([CH:43]=O)=[CH:41][CH:40]=2)[CH2:34][CH2:33]1)(=O)[CH3:30]>>[CH2:1]([N:3]([CH2:43][C:42]1[CH:45]=[CH:46][C:39]([O:38][CH:35]2[CH2:36][CH2:37][N:32]([CH2:29][CH3:30])[CH2:33][CH2:34]2)=[CH:40][CH:41]=1)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[C@@H:12]1[CH2:21][CH2:20][C:19]2[CH:18]=[C:17]([OH:22])[CH:16]=[CH:15][C:14]=2[CH2:13]1)[CH3:2]

Participants

3

Reactant 2

HCID 230875244-(1-Acetylpiperidin-4-yloxy)benzaldehydeHCID 57934253HCID 57934253, compound

Product 1

HCID 57933858(R)-6-{2-{Ethyl[4-(1-ethylpiperidin-4-yloxy)benzyl]amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 34.1%

Procedure

Synthesized from pivalic acid (R)-6-(2-ethylamino-4-methoxyphenyl)-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 described below and purified by LC-MS, the title compound (9.2 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-3805f99fca1349f0889e889c7e39b53d
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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