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

HRID 1950225Notes

Reaction equation

HRID 1950225 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].[CH3:31][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>>[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]([CH3:31])[CH2:33][CH2:34]2)=[CH:40][CH:41]=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 234332974-(1-Methylpiperidin-4-yloxy)benzaldehydeHCID 57934541pivalic acid (R)-6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 57934000(R)-6-{2-{Ethyl[4-(1-methylpiperidin-4-yloxy)benzyl]amino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 82%

Procedure

Synthesized from pivalic acid (R)-6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (35 mg) and 4-(1-methylpiperidin-4-yloxy)benzaldehyde (94 mg) according to an analogous synthetic method to Example 264 and purified by LC-MS, the title compound (37 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-89f978d2884a47abbe2f58dc2be9f95c
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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