Cyanogen Bromide → HCID 135862906, compound

HRID 1258478Notes

Reaction equation

HRID 1258478 reaction equation
[N:1]#[C:2]Br.[NH:4]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[C:6]([C:13]([NH:15][NH2:16])=[O:14])=[CH:5]1.C(=O)([O-])O.[Na+]>O.CN(C=O)C>[NH:4]1[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:7]2[C:6]([C:13]2[O:14][C:2]([NH2:1])=[N:16][N:15]=2)=[CH:5]1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 58338466HCID 58338466, compound

Product 1

HCID 135862906HCID 135862906, compoundYield 78.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

360.8 mg of cyanogen bromide is added dropwise with stirring to a mixture of 500 mg of 1-(1H-pyrrolo[2,3-b]pyridine-3-carbohydrazide, 1.192 g of sodium hydrogencarbonate in 50 ml of water and 5 ml of DMF. The reaction mixture starts to foam, and a fine precipitate forms. This is filtered off with suction after 2 hours and dried, giving 450 mg of 5-(1H-pyrrolo[2,3-b]-pyridin-3-yl)-1,3,4-oxadiazol-2-ylamine (yield: 78.8%); MS-FAB (M+H+)=202.2; Rf (polar method): 1.00 min;

Workup

  1. filtrationThis is filtered off with suction after 2 hours
  2. customdried

Sources & evidence

ORD record
ord-733e960d478f4ceb919c3a9ec64b9760
Source dataset
uspto-grants-2013_06
Patent number
US08466170B2

Reaction notes

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