Cyanogen Bromide → HCID 66930368, compound

HRID 1907823Notes

Reaction equation

HRID 1907823 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH2:18][NH2:19])[N:13]=[N:14][C:15]=1[O:16][CH3:17].[N:20]#[C:21]Br>C(O)C.O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH3:17][O:16][C:15]1[C:10]([O:9][CH3:8])=[CH:11][C:12]2[N:13]([C:21]([NH2:20])=[N:19][CH:18]=2)[N:14]=1

Participants

5

Reactant 2

HCID 10476Cyanogen Bromide3×HCID 66930092HCID 66930092, compound

Product 1

HCID 66930368HCID 66930368, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

C-(5,6-Dimethoxypyridazin-3-yl)methylamine trifluoroacetic acid salt (37 mg) was initially charged in a mixture of ethanol and water (3.75/0.75 ml) while stirring at RT. Thereafter, cyanogen bromide solution (0.1 ml; 5M in ACN) was cautiously added dropwise and the mixture was stirred at RT for 3 h. Then further cyanogen bromide solution (0.1 ml) was added and the mixture was left to stand overnight. After again adding cyanogen bromide solution (0.1 ml), the mixture was stirred for 4 h, left to stand over the weekend and then heated to 40° C. for 2 h. Subsequently, the solvent was drawn off and the residue was purified by means of preparative HPLC. The product-containing fractions were combined, freed of the acetonitrile and freeze-dried. 18 mg of the desired compound were obtained.

Workup

  1. stirringthe mixture was stirred at RT for 3 h
  2. waitthe mixture was left
  3. waitleft
  4. temperatureheated to 40° C. for 2 h
  5. customthe residue was purified by means of preparative HPLC
  6. customfreeze-dried

Sources & evidence

ORD record
ord-6fbe136973214f619a5c9a6f7adbad99
Source dataset
uspto-grants-2013_12
Patent number
US08598177B2

Reaction notes

Loading…