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}isopropylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1950367Notes

Reaction equation

HRID 1950367 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][C:38]=1[OH:39])[C:5]([N:7]([CH:33]([CH3:35])[CH3:34])[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=1[CH:16]1[CH2:25][CH2:24][C:23]2[CH:22]=[C:21]([O:26]C(=O)C(C)(C)C)[CH:20]=[CH:19][C:18]=2[CH2:17]1)=O.Cl[CH2:41][C:42]([N:44]1[CH2:53][CH2:52][C:47]2([O:51][CH2:50][CH2:49][O:48]2)[CH2:46][CH2:45]1)=O>>[O:51]1[C:47]2([CH2:52][CH2:53][N:44]([CH2:42][CH2:41][O:39][C:38]3[CH:37]=[CH:36][C:4]([CH2:5][N:7]([CH:33]([CH3:35])[CH3:34])[C:8]4[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=4[CH:16]4[CH2:25][CH2:24][C:23]5[CH:22]=[C:21]([OH:26])[CH:20]=[CH:19][C:18]=5[CH2:17]4)=[CH:3][C:2]=3[F:1])[CH2:45][CH2:46]2)[O:48][CH2:49][CH2:50]1

Participants

3

Reactant 2

HCID 438316402-Chloro-1-{1,4-dioxa-8-azaspiro[4.5]decan-8-yl}ethan-1-oneHCID 57934527Pivalic acid 6-{2-[(3-fluoro-4-hydroxybenzoyl)isopropylamino]-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 579337326-{2-{{4-[2-(1,4-Dioxa-8-azaspiro[4.5]dec-8-yl)ethoxy]-3-fluorobenzyl}isopropylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 21.9%

Procedure

Synthesized from pivalic acid 6-{2-[(3-fluoro-4-hydroxybenzoyl)isopropylamino]-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-yl ester (25 mg) and 2-chloro-1-(1,4-dioxa-8-azaspiro[4.5]dec-8-yl)ethanone (21 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (6.2 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-b1c512adc3e24d6986a60eb923835830
Source dataset
uspto-grants-2013_03
Patent number
US08399520B2

Reaction notes

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