N-bromobutanimide → 5-((4-(7-amino-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)methyl)-1,3,4-oxadiazol-2(3H)-one

HRID 2047080Notes

Reaction equation

HRID 2047080 reaction equation
[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:12]=[N:13][C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)=[CH:15][CH:16]=3)=[C:6]2[N:5]=[C:4]([CH:23]2[CH2:28][CH2:27][CH:26]([CH2:29][C:30]3[O:34][C:33](=[O:35])[NH:32][N:31]=3)[CH2:25][CH2:24]2)[CH:3]=1.FC(F)(F)C([O-])=O.[Br:43]N1C(=O)CCC1=O>CC#N>[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:12]=[N:13][C:14]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)=[CH:15][CH:16]=3)=[C:6]2[N:5]=[C:4]([CH:23]2[CH2:24][CH2:25][CH:26]([CH2:29][C:30]3[O:34][C:33](=[O:35])[NH:32][N:31]=3)[CH2:27][CH2:28]2)[C:3]=1[Br:43]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 84468TrifluoroacetateHCID 674943835-((4-(7-amino-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)methyl)-1,3,4-oxadiazol-2(3H)-one

Product 1

HCID 674943045-((4-(7-amino-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)methyl)-1,3,4-oxadiazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 20 mL scintillation vial was charged 5-((4-(7-amino-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)methyl)-1,3,4-oxadiazol-2(3H)-one as a trifluoroacetate salt (0.035 mmol, 20 mg), MeCN (2 mL) and N-bromosuccinimide (0.035 mmol, 6.3 mg). The resulting solution was stirred at room temperature for 1 hour. After 1 hour, the solvent was removed in vacuo and the resulting residue was purified via reverse-phase HPLC to yield 5-((4-(7-amino-6-bromo-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)methyl)-1,3,4-oxadiazol-2(3H)-one (m+H=546.57, retention time=4.07 min).

Workup

  1. waitAfter 1 hour
  2. customthe solvent was removed in vacuo
  3. customthe resulting residue was purified via reverse-phase HPLC

Sources & evidence

ORD record
ord-d3a7b21201e449008ae6c8dc62799c12
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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