2-Chloro-1-{1,4-dioxa-8-azaspiro[4.5]decan-8-yl}ethan-1-one → 6-{2-{{4-[2-(1,4-Dioxa-8-azaspiro[4.5]dec-8-yl)ethoxy]-3-fluorobenzyl}methylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950433Notes

Reaction equation

HRID 1950433 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.Cl[CH2:39][C:40]([N:42]1[CH2:51][CH2:50][C:45]2([O:49][CH2:48][CH2:47][O:46]2)[CH2:44][CH2:43]1)=O>>[O:49]1[C:45]2([CH2:50][CH2:51][N:42]([CH2:40][CH2:39][O:37][C:36]3[CH:35]=[CH:34][C:4]([CH2:5][CH2:7][NH:8][C:9]4[CH:14]=[C:13]([O:15][CH3:16])[CH:12]=[CH:11][C:10]=4[CH:17]4[CH2:26][CH2:25][C:24]5[CH:23]=[C:22]([OH:27])[CH:21]=[CH:20][C:19]=5[CH2:18]4)=[CH:3][C:2]=3[F:1])[CH2:43][CH2:44]2)[O:46][CH2:47][CH2:48]1

Participants

3

Reactant 2

HCID 438316402-Chloro-1-{1,4-dioxa-8-azaspiro[4.5]decan-8-yl}ethan-1-oneHCID 66626888Pivalic acid 6-{2-[(3-fluoro-4-hydroxybenzoyl)methylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 666258106-{2-{{4-[2-(1,4-Dioxa-8-azaspiro[4.5]dec-8-yl)ethoxy]-3-fluorobenzyl}methylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 36.8%

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 2-chloro-1-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)ethanone (17 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (8.4 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-82a6edf86f394844b7de6000f674a319
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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