2-chloro-N,N-dimethylacetamide → 6-{2-{[4-(2-Dimethylaminoethoxy)benzyl]methylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950416Notes

Reaction equation

HRID 1950416 reaction equation
[OH:1][C:2]1[CH:36]=[CH:35][C:5]([C:6]([CH2:8][NH:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=2[CH:18]2[CH2:27][CH2:26][C:25]3[CH:24]=[C:23]([O:28]C(=O)C(C)(C)C)[CH:22]=[CH:21][C:20]=3[CH2:19]2)=O)=[CH:4][CH:3]=1.Cl[CH2:38][C:39]([N:41]([CH3:43])[CH3:42])=O>>[CH3:42][N:41]([CH3:43])[CH2:39][CH2:38][O:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][CH2:8][NH:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=2[CH:18]2[CH2:27][CH2:26][C:25]3[CH:24]=[C:23]([OH:28])[CH:22]=[CH:21][C:20]=3[CH2:19]2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 66626427Pivalic acid 6-{2-[(4-hydroxybenzoyl)methylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 666256086-{2-{[4-(2-Dimethylaminoethoxy)benzyl]methylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 22.9%

Procedure

Synthesized from pivalic acid 6-{2-[(4-hydroxybenzoyl)methylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (25 mg) and 2-chloro-N,N-dimethylacetamide (13 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (5.4 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-c3cea1d81b4649cf9e4751aeddbf6cad
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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