2-chloro-N-ethyl-N-methylacetamide → 6-{2-{Ethyl{4-[2-(ethylmethylamino)ethoxy]benzyl}amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950401Notes

Reaction equation

HRID 1950401 reaction equation
C(N(C(=O)C1C=CC(O)=CC=1)C1[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)C.Cl[CH2:39][C:40]([N:42]([CH2:44][CH3:45])[CH3:43])=O>>[CH2:44]([N:42]([CH2:40][C:39]1[CH:19]=[CH:18][C:17]([O:22][CH2:39][CH2:40][N:42]([CH2:44][CH3:45])[CH3:43])=[CH:16][CH:15]=1)[C:43]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]([OH:22])[CH:16]=[CH:15][C:14]=2[CH2:13]1)[CH3:45]

Participants

3

Reactant 2

HCID 222346982-chloro-N-ethyl-N-methylacetamideHCID 57934562Pivalic acid 6-{2-[ethyl(4-hydroxybenzoyl)amino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 579342126-{2-{Ethyl{4-[2-(ethylmethylamino)ethoxy]benzyl}amino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 88.3%

Procedure

Synthesized from pivalic acid 6-{2-[ethyl(4-hydroxybenzoyl)amino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (20 mg) and 2-chloro-N-ethyl-N-methylacetamide (11 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (8.6 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-7e1641e149cb40d390f8bf05d10fac9f
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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