Pyridine → HCID 58032642, compound

HRID 2201006Notes

Reaction equation

HRID 2201006 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[N:14]3[N:15]=[C:16]([O:18][CH3:19])[N:17]=[C:13]3[NH:12][C:11]([CH3:20])=[C:10]2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5][CH:4]=1)#[N:2].[F:26][C:27]([F:38])([F:37])[C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=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]([O:18][CH3:19])[N:17]=[C:13]3[N:12]([C:32]3[CH:31]=[CH:30][CH:29]=[C:28]([C:27]([F:38])([F:37])[F:26])[CH:33]=3)[C:11]([CH3:20])=[C:10]2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5][CH:4]=1)#[N:2]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 27343883-(Trifluoromethyl)phenylboronic acidHCID 136133155HCID 136133155, compound

Product 1

HCID 58032642HCID 58032642, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

(rac)-Ethyl 7-(4-cyanophenyl)-2-methoxy-5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carboxylate (185 mg, 0.55 mmol), 3-(trifluoromethyl)phenylboronic acid (207 mg, 1.09 mmol, 2 eq.), anhydrous copper(II) acetate (198 mg, 1.09 mmol, 2 eq.) and molecular sieve (80 mg, 4 Å) were initially charged. Under an atmosphere of argon protective gas, abs. dichloromethane (12 ml), pyridine (176 μl, 2.18 mmol, 4 eq.) and triethylamine (152 μl, 1.09 mmol, 2 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 (103 mg, 39% 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 (103 mg, 39% of theory)

Sources & evidence

ORD record
ord-5e4196d95eb04a49b9e0b5f342ab6ef6
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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