1-(2-Chloroethyl)azepane → 6-{2-{[4-(2-Azepan-1-yl-ethoxy)benzyl]propylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1434257Notes

Reaction equation

HRID 1434257 reaction equation
[OH:1][C:2]1[CH:38]=[CH:37][C:5]([C:6]([CH2:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=2[CH:20]2[CH2:29][CH2:28][C:27]3[CH:26]=[C:25]([O:30]C(=O)C(C)(C)C)[CH:24]=[CH:23][C:22]=3[CH2:21]2)=O)=[CH:4][CH:3]=1.Cl[CH2:40][CH2:41][N:42]1[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1>>[N:42]1([CH2:41][CH2:40][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:6][CH2:8][CH2:9][CH2:10][NH:11][C:12]3[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=3[CH:20]3[CH2:29][CH2:28][C:27]4[CH:26]=[C:25]([OH:30])[CH:24]=[CH:23][C:22]=4[CH2:21]3)=[CH:37][CH:38]=2)[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]1

Participants

3

Reactant 2

HCID 166251-(2-Chloroethyl)azepaneHCID 66626482Pivalic acid 6-{2-[(4-hydroxybenzoyl)propylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 666263226-{2-{[4-(2-Azepan-1-yl-ethoxy)benzyl]propylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 28.5%

Procedure

Synthesized from pivalic acid 6-{2-[(4-hydroxybenzoyl)propylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (30 mg) and 1-(2-chloroethyl)azepane (23 mg) according to an analogous synthetic method to Example 404 and purified by NH silica gel column chromatography (hexane-ethyl acetate system), the title compound (9 mg) was obtained.

Workup

  1. custompurified by NH silica gel column chromatography (hexane-ethyl acetate system)

Sources & evidence

ORD record
ord-e76060c5a45b4537bf2e3f2e0d2b2e69
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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