Chloro-N,N-diethylacetamide → 6-{2-{[4-(2-Diethylaminoethoxy)-3-fluorobenzyl]isopropylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-ol

HRID 1434172Notes

Reaction equation

HRID 1434172 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]([CH2:47][CH3:48])[CH2:45][CH3:46])=O>>[CH2:42]([N:44]([CH2:47][CH3:48])[CH2:45][CH2:46][O:39][C:38]1[CH:37]=[CH:36][C:4]([CH2:5][N:7]([CH:33]([CH3:35])[CH3:34])[C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][C:9]=2[CH:16]2[CH2:25][CH2:24][C:23]3[CH:22]=[C:21]([OH:26])[CH:20]=[CH:19][C:18]=3[CH2:17]2)=[CH:3][C:2]=1[F:1])[CH3:41]

Participants

3

Reactant 2

HCID 16844Chloro-N,N-diethylacetamideHCID 57934527Pivalic acid 6-{2-[(3-fluoro-4-hydroxybenzoyl)isopropylamino]-4-methoxyphenyl)-5,6,7,8-tetrahydronaphthalen-2-yl ester

Product 1

HCID 579341776-{2-{[4-(2-Diethylaminoethoxy)-3-fluorobenzyl]isopropylamino}-4-methoxyphenyl}-5,6,7,8-tetrahydronaphthalen-2-olYield 31.5%

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-N,N-diethylacetamide (14 mg) according to an analogous synthetic method to Example 404 and purified by LC-MS, the title compound (7.9 mg) was obtained.

Workup

  1. custompurified by LC-MS

Sources & evidence

ORD record
ord-eda9750fdca04dfda71f9bdf008da7b7
Source dataset
uspto-grants-2009_11
Patent number
US07612114B2

Reaction notes

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