1,1'-Carbonyldiimidazole → (S)-5-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)phenyl)-1,3,4-oxadiazol-2(3H)-one

HRID 539005Notes

Reaction equation

HRID 539005 reaction equation
[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]2[N:16]=[CH:17][C:18]([C:19]3[CH:28]=[CH:27][C:22]([C:23]([NH:25][NH2:26])=[O:24])=[CH:21][CH:20]=3)=[C:12]2[N:11]=1)([CH3:3])[CH3:2].N1([C:34](N2C=CN=C2)=[O:35])C=CN=C1>CN(C=O)C.CCOC(C)=O>[CH:1]([C@H:4]1[CH2:8][O:7][C:6](=[O:9])[N:5]1[C:10]1[CH:15]=[CH:14][N:13]2[N:16]=[CH:17][C:18]([C:19]3[CH:28]=[CH:27][C:22]([C:23]4[O:24][C:34](=[O:35])[NH:26][N:25]=4)=[CH:21][CH:20]=3)=[C:12]2[N:11]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 67033928(S)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide

Product 1

HCID 67034488(S)-5-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)phenyl)-1,3,4-oxadiazol-2(3H)-oneYield 44.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)benzohydrazide (Example 9, Step 2; 91 mg, 0.239 mmol) in DMF (2 mL) was added di(1H-imidazol-1-yl)methanone (40.7 mg, 0.251 mmol). The reaction mixture was allowed to stir for 1 hour at ambient temperature, then dissolved in EtOAc, washed with water and brine, and concentrated. The resulting solid was suspended in dichloromethane, filtered, washed with dichloromethane, then concentrated to give crude product. The residue was purified by silica gel chromatography (0-5% MeOH in dichloromethane) to afford 42.8 mg (44%) of (S)-5-(4-(5-(4-isopropyl-2-oxooxazolidin-3-yl)pyrazolo[1,5-a]pyrimidin-3-yl)phenyl)-1,3,4-oxadiazol-2(3H)-one. LCMS (APCI+) m/z 407.5 [M+H]+.

Workup

  1. washwashed with water and brine
  2. concentrationconcentrated
  3. filtrationfiltered
  4. washwashed with dichloromethane
  5. concentrationconcentrated
  6. customto give crude product
  7. customThe residue was purified by silica gel chromatography (0-5% MeOH in dichloromethane)

Sources & evidence

ORD record
ord-f15841b9100c4c739d2f5fc26ccc4038
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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