Pyridine → HCID 86028266, compound

HRID 1508173Notes

Reaction equation

HRID 1508173 reaction equation
[Br:1][C:2]1[C:3]([Cl:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](O)=[O:6].Cl.[CH3:13][NH:14][O:15][CH3:16].CCN=C=NCCCN(C)C.Cl.N1C=CC=CC=1>C1COCC1>[Br:1][C:2]1[C:3]([Cl:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([N:14]([O:15][CH3:16])[CH3:13])=[O:6]

Participants

6

Reactant 4

HCID 1049PyridineHCID 331243-bromo-2-chlorobenzoic acidHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 86028266HCID 86028266, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-2-chlorobenzoic acid (1.79 mmol) in 12 mL THF were added N,O-dimethylhydroxylamine HCl (2.32 mmol), EDC.HCl (4.29 mmol) and pyridine (2.68 mmol) at 0° C. The cooling bath was removed and stirring was continued at RT overnight. The reaction was diluted with DCM and extracted with water, sat. aq. NH4Cl solution, sat. aq. NaHCO3 solution, dried over MgSO4 and concentrated in vacuo. Purification by CC (KP-SIL™ from Biotage) using Hept to EtOAc gives the desired compound as colorless oil.

Workup

  1. customThe cooling bath was removed
  2. additionThe reaction was diluted with DCM
  3. extractionextracted with water, sat. aq. NH4Cl solution, sat. aq. NaHCO3 solution
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by CC (KP-SIL™ from Biotage)

Sources & evidence

ORD record
ord-567ead448a434567a383dfdc81e26b5e
Source dataset
uspto-grants-2015_12
Patent number
US09221832B2

Reaction notes

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