Pyridine → HCID 58032657, compound

HRID 2201005Notes

Reaction equation

HRID 2201005 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[N:15]=[C:16]([CH3:18])[N:17]=[C:13]3[NH:12][C:11]([CH3:19])=[C:10]2[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:5][CH:4]=1)#[N:2].[F:25][C:26]([F:37])([F:36])[C:27]1[CH:28]=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=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]([CH3:18])[N:17]=[C:13]3[N:12]([C:31]3[CH:30]=[CH:29][CH:28]=[C:27]([C:26]([F:37])([F:36])[F:25])[CH:32]=3)[C:11]([CH3:19])=[C:10]2[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 136133153HCID 136133153, compound

Product 1

HCID 58032657HCID 58032657, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

(rac)-Ethyl 7-(4-cyanophenyl)-2,5-dimethyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate (50 mg, 0.15 mmol), 3-(trifluoromethyl)phenylboronic acid (88 mg, 0.46 mmol, 3 eq.), anhydrous copper(II) acetate (140 mg, 0.77 mmol, 5 eq.) and molecular sieve (80 mg, 4 Å) were initially charged. Under an atmosphere of argon protective gas, abs. dichloromethane (4 ml), pyridine (125 μl, 1.55 mmol, 10 eq.) and triethylamine (108 μl, 0.77 mmol, 5 eq.) were added. After 24 h of stirring, the mixture was filtered through kieselguhr 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-0.05% TFA). After lyophilization, the product was obtained as a solid (4.5 mg, 6% of theory).

Workup

  1. filtrationthe mixture was filtered through kieselguhr
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by preparative HPLC (Gromsil C18 column, 30×250 mm; mobile phase: acetonitrile-water-0.05% TFA)
  4. customAfter lyophilization, the product was obtained as a solid (4.5 mg, 6% of theory)

Sources & evidence

ORD record
ord-cbe749a1e8654df7832b0aec911edd79
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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