4-(2-Dimethylamino-2-methylpropoxy)-3-fluorobenzaldehyde → (R)-6-{2-{[4-(2-Dimethylamino-2-methylpropoxy)-3-fluorobenzyl]ethylamino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950227Notes

Reaction equation

HRID 1950227 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]([CH3:47])[C:33]([CH3:46])([CH3:45])[CH2:34][O:35][C:36]1[CH:43]=[CH:42][C:39]([CH:40]=O)=[CH:38][C:37]=1[F:44]>>[CH3:47][N:32]([CH3:31])[C:33]([CH3:45])([CH3:46])[CH2:34][O:35][C:36]1[CH:43]=[CH:42][C:39]([CH2:40][CH2:2][CH2:1][NH:3][C:4]2[CH:9]=[C:8]([O:10][CH3:11])[C:7]([O:12][CH3:13])=[CH:6][C:5]=2[C@@H:14]2[CH2:23][CH2:22][C:21]3[CH:20]=[C:19]([OH:24])[CH:18]=[CH:17][C:16]=3[CH2:15]2)=[CH:38][C:37]=1[F:44]

Participants

3

Reactant 2

HCID 230871524-(2-Dimethylamino-2-methylpropoxy)-3-fluorobenzaldehydeHCID 57934541pivalic acid (R)-6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 66627081(R)-6-{2-{[4-(2-Dimethylamino-2-methylpropoxy)-3-fluorobenzyl]ethylamino}-4,5-dimethoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 37.4%

Procedure

Synthesized from pivalic acid (R)-6-(2-ethylamino-4,5-dimethoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester (20 mg) and 4-(2-dimethylamino-2-methylpropoxy)-3-fluorobenzaldehyde (55 mg) according to an analogous synthetic method to Example 264 and purified by LC-MS, the title compound (10 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-2091ba39060143ffa7f910e4dbead575
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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