Pyridine → HCID 22040478, compound

HRID 2070326Notes

Reaction equation

HRID 2070326 reaction equation
F[C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[CH:6][CH:5]=[C:4]([N+:15]([O-])=O)[C:3]=1[NH2:18].Cl.NO.N1C=[CH:26][CH:25]=[CH:24][CH:23]=1>C(O)C>[CH:14]1([N:11]2[CH2:12][CH2:13][N:8]([C:7]3[CH:2]=[C:3]([NH2:18])[C:4]([NH2:15])=[CH:5][CH:6]=3)[CH2:9][CH2:10]2)[CH2:26][CH2:25][CH2:24][CH2:23]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 220408162-Fluoro-3-(4-methyl-piperazin-1-yl)-6-nitro-phenylamine

Product 1

HCID 22040478HCID 22040478, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 50 mL round bottom flask was charged with 1 (680 mg, 2.5 mmol), hydroxylamine HCl (191 mg, 2.75 mmol), pyridine (0.25 mL, 3.0 mmol) and ethanol (10 mL). The resulting reaction mixture was stirred at rt overnight. The crude product was concentrated, absorbed onto silica gel, and purified by flash chromatography (97:3 CH2Cl2/MeOH to give 2 as an orange solid. LCMS m/z 289.2 (MH+), tR=2.06 min.

Workup

  1. customThe resulting reaction mixture
  2. concentrationThe crude product was concentrated
  3. customabsorbed onto silica gel
  4. custompurified by flash chromatography (97:3 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-72c27f6ef43449bca9863dc89b298fc8
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

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