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

HRID 1950351Notes

Reaction equation

HRID 1950351 reaction equation
[CH2:1]([N:3]([C:29]([C:31]1[CH:36]=[CH:35][C:34]([OH:37])=[CH:33][N:32]=1)=O)[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=1[CH: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].Cl[CH2:39][C:40]([N:42]([CH3:44])[CH3:43])=O>>[CH3:43][N:42]([CH3:44])[CH2:40][CH2:39][O:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:29][N:3]([CH2:1][CH3:2])[C:4]2[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:5]=2[CH:12]2[CH2:21][CH2:20][C:19]3[CH:18]=[C:17]([OH:22])[CH:16]=[CH:15][C:14]=3[CH2:13]2)=[N:32][CH:33]=1

Participants

3

Reactant 2

HCID 758862-chloro-N,N-dimethylacetamideHCID 57934579Pivalic acid 6-{2-[ethyl(5-hydroxypyridine-2-carbonyl)amino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 579344786-{2-{[5-(2-Dimethylaminoethoxy)pyridin-2-ylmethyl]ethylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 101.4%

Procedure

Synthesized from pivalic acid 6-{2-[ethyl(5-hydroxypyridine-2-carbonyl)amino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (25 mg) and 2-chloro-N,N-dimethylacetamide (12 mg) following the synthetic method of Example 404 described below and purified by LC-MS, the title compound (24 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-690756d517a5449ab9db9b94ee111be9
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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