2-chloro-N-methyl-N-propylacetamide → (R)-6-{2-{Ethyl{4-[2-(methylpropylamino)ethoxy]benzyl}amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950512Notes

Reaction equation

HRID 1950512 reaction equation
[CH2:1]([N:3]([C:29](=O)[C:30]1[CH:35]=[CH:34][C:33]([OH:36])=[CH:32][CH:31]=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]([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]([CH3:46])[CH2:43][CH2:44][CH3:45])=O>>[CH2:1]([N:3]([CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:39][CH2:40][N:42]([CH3:46])[CH2:43][CH2:44][CH3:45])=[CH:32][CH:31]=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 230874062-chloro-N-methyl-N-propylacetamideHCID 57934043pivalic acid (R)-6-{2-[ethyl(4-hydroxybenzoyl)amino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 57934297(R)-6-{2-{Ethyl{4-[2-(methylpropylamino)ethoxy]benzyl}amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 49.2%

Procedure

Synthesized from pivalic acid (R)-6-{2-[ethyl(4-hydroxybenzoyl)amino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (15 mg) and 2-chloro-N-methyl-N-propyl acetamide (8.7 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (7.4 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-6809ef5a43414cefa898010f9ac8a982
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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