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

HRID 595433

반응식

HRID 595433 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b5f9b7339f1d48eab6d70d1c62750fa9
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242975B2

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