2-Bromobenzoyl chloride → HCID 18677533, compound

HRID 1634211Notes

Reaction equation

HRID 1634211 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([NH2:9])[N:6]=[C:5]([NH2:10])[CH:4]=1.[Br:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14](Cl)=[O:15]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Br:11][C:12]1[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=1[C:14]([NH:1][CH2:2][C:3]1[CH:8]=[C:7]([NH2:9])[N:6]=[C:5]([NH2:10])[CH:4]=1)=[O:15]

Participants

5

Reactant 2

HCID 235422-Bromobenzoyl chlorideHCID 18677512HCID 18677512, compound

Product 1

HCID 18677533HCID 18677533, compoundYield 20.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

A solution of 172.5 mg (1.25 mmol) 4-aminomethyl-pyridine-2,6-diamine in 5 ml pyridine was treated with 275 mg (1.25 mmol) o-bromobenzoylchloride and a catalytic amount 4-dimethylaminopyridine and stirred for 2.5 h at room temperature. The mixture was evaporated to dryness and the residue was purified by column chromatography on silica eluting with dichloromethane/methanol 9/1 to yield 81 mg (20%) of the title compound.

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe residue was purified by column chromatography on silica eluting with dichloromethane/methanol 9/1

Sources & evidence

ORD record
ord-b13599286e134570b356cb774f84d2b3
Source dataset
uspto-grants-2003_01
Patent number
US06506772B1

Reaction notes

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