Acetic Acid → HCID 58447001, compound

HRID 1045743Notes

Reaction equation

HRID 1045743 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[N:6][C:5]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)=[C:4]([NH:16][NH2:17])[N:3]=1.CC(O)=O.[N:22]([O-])=O.[Na+]>O.C([O-])(O)=O.[Na+]>[Br:1][C:2]1[N:3]2[N:22]=[N:17][N:16]=[C:4]2[C:5]([N:9]2[CH2:10][CH2:11][N:12]([CH3:15])[CH2:13][CH2:14]2)=[N:6][C:7]=1[CH3:8]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 23668193Sodium NitriteHCID 58447017HCID 58447017, compound

Product 1

HCID 58447001HCID 58447001, compoundYield 76.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
10 °C

Procedure

A 25 mL round bottom flask was charged with 2-bromo-6-hydrazinyl-3-methyl-5-(4-methylpiperazin-1-yl)pyrazine (0.92 g, 3.0 mmol) and CH3COOH (2 mL). To the above was added dropwise a solution of NaNO2 (0.32 g, 4.6 mmol) in water (2 mL) at 10° C. The resulting mixture was stirred at 10° C. for 1 h. Work-up: the reaction mixture was diluted with saturated aqueous NaHCO3 (100 mL) and then extracted with CH2Cl2 (100 mL×3). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with 4% MeOH in CH2Cl2, to afford 0.72 g (75%) of the product as a white solid. MS m/z: 312 (M+H+).

Workup

  1. extractionextracted with CH2Cl2 (100 mL×3)
  2. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel with 4% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-4badc0ef664d4ea99833150324852d4d
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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