4-Aminopyridine → HCID 19683068, compound

HRID 268974Notes

Reaction equation

HRID 268974 reaction equation
[Br:1][C:2]1[S:6][C:5]([S:7](Cl)(=[O:9])=[O:8])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[N:15]1[CH:16]=[CH:17][C:12]([NH:11][S:7]([C:5]2[S:6][C:2]([Br:1])=[CH:3][CH:4]=2)(=[O:9])=[O:8])=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 17274-AminopyridineHCID 27339245-Bromothiophene-2-sulfonyl chloride

Product 1

HCID 19683068HCID 19683068, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 5-bromo-thiophene-2sulphonyl chloride (1.31 g, 5.0 mmol), 4-dimethylamino-pyridine (0.61 g, 5.0 mmol) and 4-amino-pyridine (0.71 g, 7.5 mmol) in pyridine (20 ml) was stirred at 50° C. for 16 h. THE reaction mixture was evaporated and diluted with dichloromethane/MeOH/NH4OH 80:10:1. The formed precipitate was collected by filtration to yield the title compound (1.53 g, 96%) as an off-white solid, which was used without further purification. MS (ISN) 317.0 [(M−H)−], mp 310° C.

Workup

  1. customTHE reaction mixture was evaporated
  2. additiondiluted with dichloromethane/MeOH/NH4OH 80:10:1
  3. filtrationThe formed precipitate was collected by filtration

Sources & evidence

ORD record
ord-a3b2407bd98a4e66ae2cb940cde8ff75
Source dataset
uspto-grants-2008_11
Patent number
US07446113B2

Reaction notes

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