Potassium Carbonate → HCID 5279912, compound

HRID 1394431Notes

Reaction equation

HRID 1394431 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[C:8]([C:11](=[O:29])[C:12]([N:14]3[CH2:19][CH2:18][C:17](=[C:20]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:21]#[N:22])[CH2:16][CH2:15]3)=[O:13])=[CH:9][NH:10][C:3]=12.[NH:30]1[CH:34]=[CH:33][N:32]=[N:31]1.C([O-])([O-])=O.[K+].[K+]>CO.[Cu]>[O:29]=[C:11]([C:8]1[C:4]2=[N:5][CH:6]=[CH:7][C:2]([N:31]3[N:32]=[CH:33][CH:34]=[N:30]3)=[C:3]2[NH:10][CH:9]=1)[C:12]([N:14]1[CH2:19][CH2:18][C:17](=[C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:21]#[N:22])[CH2:16][CH2:15]1)=[O:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 5279908HCID 5279908, compoundHCID 178418936HCID 178418936, compound

Product 1

HCID 5279912HCID 5279912, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of compound of example 101 (34 mg, 0.084 mmol), 1,2,3-triazole (0.40 mL, 6.9 mmol), copper metal (5.4 mg, 0.084 mmol), and K2CO3 (11.5 mg, 0.083 mmol) in a sealed tube was heated at 160° C. for 5 h. The reaction mixture was diluted with MeOH (2 mL), filtered through Celite and concentrated. The residue was purified by preparative HPLC to yield title compound (3.1 mg, 0.026 mmol, 39%) as a yellow solid.

Workup

  1. filtrationfiltered through Celite
  2. concentrationconcentrated
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-4aa5c5e8105f4059938a681e161c021e
Source dataset
uspto-grants-2008_03
Patent number
US07348337B2

Reaction notes

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