Cyanogen Bromide → HCID 11154036, compound

HRID 2102413Notes

Reaction equation

HRID 2102413 reaction equation
[N:1]#[C:2]Br.[Br:4][C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:13]([C:22]([NH:24][NH2:25])=[O:23])=[N:14][C:15]3[N:16]([N:19]=[CH:20][CH:21]=3)[C:17]=2[F:18])=[C:7]([F:26])[CH:6]=1.C([O-])(O)=O.[Na+]>O1CCOCC1.O>[NH2:1][C:2]1[O:23][C:22]([C:13]2[C:12]([NH:11][C:8]3[CH:9]=[CH:10][C:5]([Br:4])=[CH:6][C:7]=3[F:26])=[C:17]([F:18])[N:16]3[N:19]=[CH:20][CH:21]=[C:15]3[N:14]=2)=[N:24][N:25]=1

Participants

6

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 69003138HCID 69003138, compound

Product 1

HCID 11154036HCID 11154036, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Cyanogen bromide (2.02 equivalents) is added to a suspension of 6-(4-bromo-2-fluorophenylamino)-7-fluoropyrazolo[1,5-a]pyrimidine-5-carboxylic acid hydrazide (1.00 equivalent) in dioxane followed by an aqueous NaHCO3 solution (1.01 equivalents). After 17 hours, the reaction mixture is diluted with water and extracted with EtOAc. The combined organic extracts are washed with brine, dried (MgSO4) and concentrated under reduced pressure. The product is purified by flash chromatography as necessary.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic extracts are washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe product is purified by flash chromatography as necessary

Sources & evidence

ORD record
ord-cf604e14ab5c47dab0f584ec048069c4
Source dataset
uspto-grants-2009_08
Patent number
US07576072B2

Reaction notes

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