Dimethylformamide → HCID 58951429, compound

HRID 1445755Notes

Reaction equation

HRID 1445755 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

HCID 58951429HCID 58951429, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

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)

Workup

  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

Sources & evidence

ORD record
ord-0fe51d26929a4bb588d1a1c741c6a049
Source dataset
uspto-grants-2010_02
Patent number
US07666871B2

Reaction notes

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