Cyanogen Bromide → HCID 25057012, compound

HRID 1690046Notes

Reaction equation

HRID 1690046 reaction equation
[N:1]#[C:2]Br.Cl.[CH3:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH3:12])[C:7]=1[NH:13][C:14]1[N:18]2[CH:19]=[C:20]([F:23])[CH:21]=[CH:22][C:17]2=[N:16][C:15]=1[C:24]1[CH:33]=[CH:32][CH:31]=[CH:30][C:25]=1[C:26]([NH:28][NH2:29])=[O:27].C(=O)([O-])O.[Na+]>O>[NH2:1][C:2]1[O:27][C:26]([C:25]2[CH:30]=[CH:31][CH:32]=[CH:33][C:24]=2[C:15]2[N:16]=[C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][N:18]3[C:14]=2[NH:13][C:7]2[C:8]([CH3:12])=[CH:9][CH:10]=[CH:11][C:6]=2[CH3:5])=[N:28][N:29]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 516892Sodium BicarbonateHCID 66902076HCID 66902076, compound

Product 1

HCID 25057012HCID 25057012, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.4 16.9 mg (0.160 mmol) of cyanogen bromide are added to a solution of 60 mg (0.141 mmol) of 2-[3-(2,6-dimethylphenylamino)-6-fluoro-imidazo[1,2-a]pyridin-2-yl]benzohydrazide hydrochloride and 29.4 mg (0.350 mmol) of sodium hydrogencarbonate in 10 ml of water, and the mixture is stirred at RT for 2 hours. The precipitated product is filtered off with suction, dried and purified by preparative thin-layer chromatography, giving 10 mg (17%) of {2-[2-(5-amino-1,3,4-oxadiazol-2-yl)phenyl]-6-fluoroimidazo[1,2-a]pyridin-3-yl}-(2,6-dimethylphenyl)amine (“B1”) as solid; MS-FAB (M+H+)=415.8; Rf (HPLC, polar method): 1.07 min.;

Workup

  1. filtrationThe precipitated product is filtered off with suction
  2. customdried
  3. custompurified by preparative thin-layer chromatography

Sources & evidence

ORD record
ord-ac916e067cdf43debf268ea5bc5f50ba
Source dataset
uspto-grants-2012_04
Patent number
US08153649B2

Reaction notes

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