2,3-Dichloropyrazine → HCID 178478364, compound

HRID 707234Notes

Reaction equation

HRID 707234 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@H:11]1[CH2:14][C@H:13]([NH2:15])[CH2:12]1.[Cl:16][C:17]1[C:22](Cl)=[N:21][CH:20]=[CH:19][N:18]=1>C(O)(C)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C@H:11]1[CH2:12][C@H:13]([NH:15][C:22]2[C:17]([Cl:16])=[N:18][CH:19]=[CH:20][N:21]=2)[CH2:14]1

Participants

4

Reactant 2

HCID 785752,3-DichloropyrazineHCID 178511738HCID 178511738, compound2×

Product 1

HCID 178478364HCID 178478364, compoundYield 67.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
150 °C

Procedure

Trans-N1-(benzo[d]thiazol-2-yl)cyclobutane-1,3-diamine (intermediate 11, 0.058 g, 0.264 mmol) and 2,3-dichloropyrazine (0.035 ml, 0.336 mmol) were suspended in isopropanol (1 mL) in a microwave vial. The mixture was heated at 150° C. for 90 minutes. The mixture was evaporated to dryness under reduced pressure and purified using silica chromatography (hexane to ethyl acetate gradient) to give trans-N1-(benzo[d]thiazol-2-yl)-N3-(3-chloropyrazin-2-yl)cyclobutane-1,3-diamine (0.0594 g, 0.179 mmol, 67.7% yield) as an oil.

Workup

  1. customThe mixture was evaporated to dryness under reduced pressure
  2. custompurified

Sources & evidence

ORD record
ord-ac09a8b186e84f14bd1828c351aa4e14
Source dataset
uspto-grants-2015_11
Patent number
US09174992B2

Reaction notes

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