Potassium Carbonate → HCID 90415200, compound

HRID 2271482Notes

Reaction equation

HRID 2271482 reaction equation
Br[CH2:2][C:3]1[N:4]=[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=2)[C:6]([O:9][CH3:10])=[N:7][CH:8]=1.[NH:18]1[CH:22]=[N:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[N:19]1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(Cl)Cl>[Cl:17][C:13]1[CH:12]=[C:11]([C:5]2[N:4]=[C:3]([CH2:2][N:18]3[CH:22]=[N:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[N:19]3)[CH:8]=[N:7][C:6]=2[O:9][CH3:10])[CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 90415072HCID 90415072, compound2×HCID 178499122HCID 178499122, compound

Product 1

HCID 90415200HCID 90415200, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(bromomethyl)-3-(3-chlorophenyl)-2-methoxypyrazine (Intermediate 3, 200.00 mg, 0.64 mmol), in acetone (3.19 mL), was added methyl 1H-1,2,4-triazole-3-carboxylate (121.60 mg, 0.96 mmol) and potassium carbonate (264.44 mg, 1.91 mmol). The reaction was stirred at room temperature for 2 h. The LCMS showed two peaks with [M+H] values consistent with the two major regioproducts. The mixture was diluted with DCM (5 mL), dried (Na2SO4) and concentrated under reduced pressure. Purification (FCC, SiO2, 20-100% EtOAc/hexanes) afforded the title compound (100 mg; 44%). 1H NMR (400 MHz, CD3OD) δ 8.79 (s, 1H), 8.26 (s, 1H), 8.01 (td, J=1.1, 2.1 Hz, 1H), 7.99-7.90 (m, 1H), 7.45-7.36 (m, 2H), 5.64 (s, 2H), 4.07 (s, 3H), 3.92 (s, 3H). [M+H]=360.24.

Workup

  1. dry with materialdried (Na2SO4)
  2. concentrationconcentrated under reduced pressure
  3. customPurification (FCC, SiO2, 20-100% EtOAc/hexanes)

Sources & evidence

ORD record
ord-bc84c790bdab42409c24b915e441d0c3
Source dataset
uspto-grants-2015_09
Patent number
US09120770B2

Reaction notes

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