1-(Chloroacetyl)azocane → 6-{2-{[4-(2-Azocan-1-ylethoxy)-3-fluorobenzyl]methylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1434244Notes

Reaction equation

HRID 1434244 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:34]=[CH:35][C:36]=1[OH:37])[C:5]([CH2:7][NH:8][C:9]1[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=1[CH:17]1[CH2:26][CH2:25][C:24]2[CH:23]=[C:22]([O:27]C(=O)C(C)(C)C)[CH:21]=[CH:20][C:19]=2[CH2:18]1)=O.[N:38]1([C:46](=O)[CH2:47]Cl)[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1>>[N:38]1([CH2:46][CH2:47][O:37][C:36]2[CH:35]=[CH:34][C:4]([CH2:5][CH2:7][NH:8][C:9]3[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=3[CH:17]3[CH2:26][CH2:25][C:24]4[CH:23]=[C:22]([OH:27])[CH:21]=[CH:20][C:19]=4[CH2:18]3)=[CH:3][C:2]=2[F:1])[CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]1

Participants

3

Reactant 2

HCID 162268991-(Chloroacetyl)azocaneHCID 66626888Pivalic acid 6-{2-[(3-fluoro-4-hydroxybenzoyl)methylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 666273876-{2-{[4-(2-Azocan-1-ylethoxy)-3-fluorobenzyl]methylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 31.9%

Procedure

Synthesized from pivalic acid 6-{2-[(3-fluoro-4-hydroxybenzoyl)methylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (20 mg) and 1-azocan-1-yl-2-chloroethanone (15 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (6.9 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-5b5e87664c134a849dee9c1d2c37c5dd
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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