1,1'-Carbonyldiimidazole → 5-(6-chloro-4-(isopropylamino)pyridin-3-yl)-1,3,4-oxadiazol-2(3H)-one

HRID 595433Notes

Reaction equation

HRID 595433 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])[C:5]([C:6]([NH:8][NH2:9])=[O:7])=[CH:4][N:3]=1.C1N=CN([C:21](N2C=NC=C2)=[O:22])C=1>CN(C=O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:6]2[O:7][C:21](=[O:22])[NH:9][N:8]=2)=[C:10]([NH:12][CH:13]([CH3:15])[CH3:14])[CH:11]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 896896686-Chloro-4-(isopropylamino)nicotinohydrazide

Product 1

HCID 896908095-(6-chloro-4-(isopropylamino)pyridin-3-yl)-1,3,4-oxadiazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-chloro-4-(isopropylamino)nicotinohydrazide (10) (800 mg, 3.5 mmol) was taken in DMF (4 mL). Added CDI (3.8 mmol, 1.1 equiv.) and stirred at room temperature for overnight. The reaction mass was concentrated under reduced pressure to remove excess of DMF. The residue was diluted using EtOAc, washed the EtOAc layer with water followed by brine solution. Collected the EtOAc layer, dried over Na2SO4, filtered and concentrated. The crude material obtained was taken to next step as such, without purification. LC/MS: Acquity BEH C18 2.1×50 mm, 1.8 micron; Solvent A=0.1% TFA in water; Solvent B=0.1% TFA in ACN; gradient 0-100% B over 2 min; retention time: 0.76 min; LCMS (ES-API), m/z 255.6 (M+H).

Workup

  1. concentrationThe reaction mass was concentrated under reduced pressure
  2. customto remove excess of DMF
  3. additionThe residue was diluted
  4. washwashed the EtOAc layer with water
  5. customCollected the EtOAc layer
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-b5f9b7339f1d48eab6d70d1c62750fa9
Source dataset
uspto-grants-2016_01
Patent number
US09242975B2

Reaction notes

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