Triethylamine → HCID 18401616, compound

HRID 1018583Notes

Reaction equation

HRID 1018583 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:6]([N:8]1[CH2:25][CH2:24][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[CH2:14][NH:13][C:12]2=[O:23])[CH2:10][CH2:9]1)=[O:7].[N:35]1[CH:40]=[CH:39][CH:38]=[C:37](B(O)O)[CH:36]=1.C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[F:32][C:29]([F:31])([F:30])[C:27]1[CH:26]=[C:5]([CH:4]=[C:3]([C:2]([F:1])([F:33])[F:34])[CH:28]=1)[C:6]([N:8]1[CH2:9][CH2:10][C:11]2([N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[CH2:14][N:13]([C:37]3[CH:36]=[N:35][CH:40]=[CH:39][CH:38]=3)[C:12]2=[O:23])[CH2:24][CH2:25]1)=[O:7]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27343783-Pyridinylboronic acidHCID 18401647HCID 18401647, compound

Product 1

HCID 18401616HCID 18401616, compoundYield 41.2%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

8-(3,5-Bis-trifluoromethyl-benzoyl)-1-(2-chloro-phenyl)-1,3,8-triaza-spiro[4.5]decan-4-one (253 mg) was dissolved in dichloromethane (5 mL), 3-pyridineboronic acid (246 mg), triethylamine (101 mg) and copper(II)-acetate (136 mg) were added. The mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was purified by chromatography on silica gel (hexane/ethylacetate=2:1) to yield the desired product (120 mg, 41%), MS: m/e=583.0 (M+H+).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by chromatography on silica gel (hexane/ethylacetate=2:1)

Sources & evidence

ORD record
ord-8392f92cf73148dfb5b2fb9554193270
Source dataset
uspto-grants-2002_11
Patent number
US06482829B2

Reaction notes

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