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

HRID 595433

反応式

HRID 595433 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b5f9b7339f1d48eab6d70d1c62750fa9
出典データセット
uspto-grants-2016_01
特許番号
US09242975B2

関連ノート

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