1,1'-Carbonyldiimidazole → 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

HRID 2047079Notes

Reaction equation

HRID 2047079 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]([NH:32][NH2:33])=[O:31])[CH2:25][CH2:24]2)[CH:3]=1.[C:34](N1C=CN=C1)(N1C=CN=C1)=[O:35]>C1COCC1>[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[CH2:24][CH2:25][CH:26]([CH2:29][C:30]3[O:31][C:34](=[O:35])[NH:33][N:32]=3)[CH2:27][CH2:28]2)[CH:3]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 469463452-(4-(7-Amino-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetohydrazide

Product 1

HCID 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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 20 mL scintillation vial was charged 2-(4-(7-amino-3-(6-phenylpyridin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)cyclohexyl)acetohydrazide (0.12 mmol), THF (5 mL), and 1,1′-carbonyldiimidazole (0.12 mmol, 25 mg). The resulting solution was stirred at room temperature for 2 hours. After 2 hours, the solvent was removed in vacuo and the residue taken up in 3:1 DMSO:MeCN. The solids are removed via centrifugation, and the title compound was purified via reverse-phase HPLC.

Workup

  1. waitAfter 2 hours
  2. customthe solvent was removed in vacuo
  3. customThe solids are removed via centrifugation
  4. customthe title compound was purified via reverse-phase HPLC

Sources & evidence

ORD record
ord-26ae59469aab4d2a8f0ce2b2f66f8768
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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