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

HRID 2423944Notes

Reaction equation

HRID 2423944 reaction equation
[OH:1][C:2]1[CH:38]=[CH:37][C:5]([C:6]([N:8]([CH:34]([CH3:36])[CH3:35])[C:9]2[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=2[CH:17]2[CH2:26][CH2:25][C:24]3[CH:23]=[C:22]([O:27]C(=O)C(C)(C)C)[CH:21]=[CH:20][C:19]=3[CH2:18]2)=O)=[CH:4][CH:3]=1.[N:39]1([C:43](=O)[CH2:44]Cl)[CH2:42][CH2:41][CH2:40]1>>[N:39]1([CH2:43][CH2:44][O:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:6][N:8]([CH:34]([CH3:36])[CH3:35])[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:37][CH:38]=2)[CH2:42][CH2:41][CH2:40]1

Participants

3

Reactant 2

HCID 25431591-(Azetidin-1-yl)-2-chloroethan-1-oneHCID 57933955Pivalic acid 6-{2-[(4-hydroxybenzoyl)isopropylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 579344656-{2-{[4-(2-Azetidin-1-ylethoxy)benzyl]isopropylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 20.2%

Procedure

Synthesized from pivalic acid 6-{2-[(4-hydroxybenzoyl)isopropylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (27 mg) and 1-azetidin-1-yl-2-chloroethanone (15 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (5.3 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-fa06777f65444ca9b7192b50a8a5c600
Source dataset
uspto-grants-2011_06
Patent number
US07960412B2

Reaction notes

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