Methanol → 7-(2,3-Dichlorobenzyl)-3-pyrazin-2-yl-6,7-dihydro[1,2,4]triazolo[4,3-a]pyrazin-8(5H)-one

HRID 576712Notes

Reaction equation

HRID 576712 reaction equation
[N:1]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[C:7]1[N:11]2[CH2:12][CH2:13][NH:14][C:15](=[O:16])[C:10]2=[N:9][N:8]=1.C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[C:26]=1[Cl:32].CO>CN(C=O)C>[Cl:32][C:26]1[C:27]([Cl:31])=[CH:28][CH:29]=[CH:30][C:25]=1[CH2:24][N:14]1[CH2:13][CH2:12][N:11]2[C:7]([C:2]3[CH:3]=[N:4][CH:5]=[CH:6][N:1]=3)=[N:8][N:9]=[C:10]2[C:15]1=[O:16]

Participants

6

Reactant 4

HCID 887MethanolHCID 10796Cesium carbonateHCID 27346021-(Bromomethyl)-2,3-dichlorobenzeneHCID 904025243-(pyrazin-2-yl)-6,7-dihydro-[1,2,4]triazolo[4,3-a]pyrazin-8(5H)-one

Product 1

HCID 862792797-(2,3-Dichlorobenzyl)-3-pyrazin-2-yl-6,7-dihydro[1,2,4]triazolo[4,3-a]pyrazin-8(5H)-oneYield 88.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a slurry of Intermediate 1 (60 mg, 0.18 mmol) and cesium carbonate (237 mg, 0.73 mmol) in DMF (1.4 mL) was added 1-(bromomethyl)-2,3-dichlorobenzene (65 mg, 0.27 mmol). After 5 h, the reaction was quenched with sat aq NH4Cl, poured into brine, and extracted with 20% IPA/CHCl3 (×3). The combined organic extracts were dried (Na2SO4), filtered, and concentrated to give a brown sludge. Trituration with MeOH provided the desired product as a beige powder (60 mg, 88%). MS (ESI): mass calcd. for C16H12Cl2N6O, 374.0; m/z found, 375.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 9.41 (s, 1H), 8.77 (s, 2H), 7.57 (dd, J=7.9, 1.2 Hz, 1H), 7.49-7.38 (m, 1H), 7.33 (t, J=7.9 Hz, 1H), 4.86-4.75 (m, 4H), 3.90-3.81 (m, 2H).

Workup

  1. customthe reaction was quenched with sat aq NH4Cl
  2. additionpoured into brine
  3. extractionextracted with 20% IPA/CHCl3 (×3)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a brown sludge

Sources & evidence

ORD record
ord-a2e757886df6408ea65ab4f7a1c17b8b
Source dataset
uspto-grants-2015_05
Patent number
US09040534B2

Reaction notes

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