Pyridine → HCID 58032631, compound

HRID 2201004Notes

Reaction equation

HRID 2201004 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[N:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=[C:13]3[NH:12][C:11]([CH3:23])=[C:10]2[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:5][CH:4]=1)#[N:2].[F:29][C:30]([F:41])([F:40])[C:31]1[CH:32]=[C:33](B(O)O)[CH:34]=[CH:35][CH:36]=1.N1C=CC=CC=1.C(N(CC)CC)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.ClCCl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[N:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=[C:13]3[N:12]([C:35]3[CH:34]=[CH:33][CH:32]=[C:31]([C:30]([F:41])([F:40])[F:29])[CH:36]=3)[C:11]([CH3:23])=[C:10]2[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 136133158HCID 136133158, compound

Product 1

HCID 58032631HCID 58032631, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

(rac)-Diethyl 7-(4-cyanophenyl)-5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-2,6-dicarboxylate (200 mg, 0.52 mmol), 3-(trifluoromethyl)phenylboronic acid (199 mg, 1.05 mmol, 2 eq.), anhydrous copper(II) acetate (190 mg, 1.05 mmol, 2 eq.) and molecular sieve (500 mg, 4 Å) were initially charged. Under an atmosphere of argon protective gas, abs. dichloromethane (5 ml), pyridine (170 μl, 2.10 mmol, 4 eq.) and triethylamine (146 μl, 1.05 mmol, 2 eq.) were added. After 24 h of stirring, the mixture was filtered through kieselguhr, the filter residue was washed with dichloromethane and the filtrate was concentrated under reduced pressure. The residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA). After lyophilization, the product was obtained as a solid (32.7 mg, 12% of theory).

Workup

  1. filtrationthe mixture was filtered through kieselguhr
  2. washthe filter residue was washed with dichloromethane
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.1% TFA)
  5. customAfter lyophilization, the product was obtained as a solid (32.7 mg, 12% of theory)

Sources & evidence

ORD record
ord-4d96f7b1737c49c7bdb7eeb048356431
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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