Acetic Acid → HCID 178480783, compound

HRID 1045769Notes

Reaction equation

HRID 1045769 reaction equation
[Br:1][C:2]1[C:3]([NH2:16])=[C:4]([NH2:15])[C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.CC(O)=O.[N:21]([O-])=O.[Na+].C([O-])([O-])=O.[Na+].[Na+]>O>[Br:1][C:2]1[C:3]2[NH:16][N:21]=[N:15][C:4]=2[C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 23668193Sodium NitriteHCID 584469905-Bromo-2-(4-methyl-1-piperazinyl)-3,4-pyridinediamine

Product 1

HCID 178480783HCID 178480783, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

A 250 mL round bottom flask was charged with 5-bromo-2-(4-methylpiperazin-1-yl)pyridine-3,4-diamine (1.2 g, 4.2 mmol) and CH3COOH (10 mL). To the above was added dropwise a solution of NaNO2 (0.30 g, 4.3 mmol) in water (1 mL) at 10° C. The resulting mixture was stirred at 10° C. for 1 h. Work-up: the reaction mixture was basified to pH 8 by saturated aqueous Na2CO3 and extracted with ethyl acetate (30 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 10% MeOH in CH2Cl2, to afford 1.1 g (88%) of the product as a white solid. MS m/z: 297 (M+H+).

Workup

  1. extractionextracted with ethyl acetate (30 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 10% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-a36dd458d7b7414aab4606f2ade2f313
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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