1-(Azetidin-1-yl)-2-chloroethan-1-one → 6-{2-{[4-(2-Azetidin-1-ylethoxy)benzyl]methylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1434230Notes

Reaction equation

HRID 1434230 reaction equation
[OH:1][C:2]1[CH:36]=[CH:35][C:5]([C:6]([CH2:8][NH:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=2[CH:18]2[CH2:27][CH2:26][C:25]3[CH:24]=[C:23]([O:28]C(=O)C(C)(C)C)[CH:22]=[CH:21][C:20]=3[CH2:19]2)=O)=[CH:4][CH:3]=1.[N:37]1([C:41](=O)[CH2:42]Cl)[CH2:40][CH2:39][CH2:38]1>>[N:37]1([CH2:41][CH2:42][O:1][C:2]2[CH:36]=[CH:35][C:5]([CH2:6][CH2:8][NH:9][C:10]3[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:11]=3[CH:18]3[CH2:27][CH2:26][C:25]4[CH:24]=[C:23]([OH:28])[CH:22]=[CH:21][C:20]=4[CH2:19]3)=[CH:4][CH:3]=2)[CH2:40][CH2:39][CH2:38]1

Participants

3

Reactant 2

HCID 25431591-(Azetidin-1-yl)-2-chloroethan-1-oneHCID 66626427Pivalic acid 6-{2-[(4-hydroxybenzoyl)methylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 666272666-{2-{[4-(2-Azetidin-1-ylethoxy)benzyl]methylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 19.8%

Procedure

Synthesized from pivalic acid 6-{2-[(4-hydroxybenzoyl)methylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (25 mg) and 1-azetidin-1-yl-2-chloroethanone (14 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (4.8 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-4ade2d6839e64c4cbc518419a7ba7030
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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