Triethylamine → 8-(3,5-Bis-trifluoromethyl-benzoyl)-1-phenyl-3-pyridin-4-yl-1,3,8-triaza-spiro[4.5]decan-4-one

HRID 1018571Notes

Reaction equation

HRID 1018571 reaction equation
[F:1][C:2]([F:33])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[C:6]([N:8]1[CH2:24][CH2:23][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:14][NH:13][C:12]2=[O:22])[CH2:10][CH2:9]1)=[O:7].[N:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1.C(N(CC)CC)C>ClCCl>[F:33][C:2]([F:1])([F:32])[C:3]1[CH:4]=[C:5]([CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:27]=1)[C:6]([N:8]1[CH2:9][CH2:10][C:11]2([N:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:14][N:13]([C:37]3[CH:38]=[CH:39][N:34]=[CH:35][CH:36]=3)[C:12]2=[O:22])[CH2:23][CH2:24]1)=[O:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2734379(Pyridin-4-yl)boronic acidHCID 184017258-(3,5-Bis-trifluoromethyl-benzoyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one

Product 1

HCID 102308908-(3,5-Bis-trifluoromethyl-benzoyl)-1-phenyl-3-pyridin-4-yl-1,3,8-triaza-spiro[4.5]decan-4-oneYield 22.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 8-(3,5-bis-trifluoromethyl-benzoyl)-1-phenyl-1,3,8-triaza-spiro[4.5]decan-4-one (0.1 g, 0.21 mmol), 4-pyridylboronic acid (52 mg, 0.42 mmol), cupric acetate (58 mg, 0.32 mmol) and triethylamine (60 μL, 0.42 mmol) in dichloromethane (2 mL) was stirred for 2 d at room temperature. Chromatography on silica gel (ethyl acetate) yielded the desired product (26 mg, 21%), MS: m/e=549.1 (M+H+).

Sources & evidence

ORD record
ord-0c1380d7b94d446eb20222446d46652a
Source dataset
uspto-grants-2002_11
Patent number
US06482829B2

Reaction notes

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