Dimethylformamide → HCID 58951429、化合物

HRID 1445755ノート

反応式

HRID 1445755 の反応式
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[CH:15][C:14]([C:17]3[O:18][C:19]([CH3:26])=[C:20]([CH2:22][C:23]([O-])=[O:24])[N:21]=3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[Na+].[C:28](Cl)(=O)C(Cl)=O.CN(C)C=O.C[N:40]1[CH2:45][CH2:44]O[CH2:42][CH2:41]1>O1CCOCC1.ClCCl>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[CH:15][C:14]([C:17]3[O:18][C:19]([CH3:26])=[C:20]([CH2:22][C:23]([N:40]4[CH2:41][CH2:42][CH2:28][C@H:45]4[CH3:44])=[O:24])[N:21]=3)=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:3])=[O:4]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 79724-MethylmorpholineHCID 65578Oxalyl chlorideHCID 86614632Sodium {2-[6-(4-methanesulfonyl-phenyl)-pyridin-3-yl]-5-methyl-oxazol-4-yl}-acetate2 回

生成物 1

HCID 58951429HCID 58951429、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a stirring solution of Sodium {2-[6-(4-methanesulfonyl-phenyl)-pyridin-3-yl]-5-methyl-oxazol-4-yl}-acetate (See Intermediate 20) (1.0 mmol) and oxalyl chloride (3.0 mmol) in dioxane (0.10M), add a catalytic amount of dimethylformamide and heat to reflux for 30 minutes. After this time, remove the heat and concentrate in vacuo. Take the resulting solid into dichloromethane (0.10M) and slowly add a solution of (R)-methyl-pyrrolidine hydrochloride (1.0 mmol) and n-methylmorpholine (2.0 mmol) in dichloromethane. Stir at room temperature for 1 hour. After this time, the reaction appears complete. Wash the reaction with 1N hydrochloric acid while extracting with dichloromethane. Concentrate the organic layer in vacuo and purify via radial chromatography eluting with methanol and dichloromethane. MS (m/e): 440.2(M+1)

後処理

  1. temperatureheat
  2. temperatureto reflux for 30 minutes
  3. customAfter this time, remove the
  4. temperatureheat
  5. concentrationconcentrate in vacuo
  6. washWash
  7. customthe reaction with 1N hydrochloric acid
  8. extractionwhile extracting with dichloromethane
  9. concentrationConcentrate the organic layer in vacuo
  10. custompurify via radial chromatography
  11. washeluting with methanol and dichloromethane

出典と根拠

ORDレコード
ord-0fe51d26929a4bb588d1a1c741c6a049
出典データセット
uspto-grants-2010_02
特許番号
US07666871B2

反応ノート

読み込み中…