Triethylamine → HCID 22558381, compound

HRID 984436Notes

Reaction equation

HRID 984436 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].FC(F)(F)C(O)=O.[NH2:13][C:14]1[CH:15]=[C:16]([NH:20][C:21](=[O:38])[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[O:35][CH:34]=[N:33][CH:32]=3)=[C:27]([O:36][CH3:37])[CH:26]=2)=[O:23])[CH:17]=[CH:18][CH:19]=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)C>[CH3:1][S:2]([NH:13][C:14]1[CH:15]=[C:16]([NH:20][C:21](=[O:38])[C:22]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:31]3[O:35][CH:34]=[N:33][CH:32]=3)=[C:27]([O:36][CH3:37])[CH:26]=2)=[O:23])[CH:17]=[CH:18][CH:19]=1)(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 22558371HCID 22558371, compound

Product 1

HCID 22558381HCID 22558381, compoundYield 105.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

12 mg (0.011 mmol) of methanesulphonyl chloride were added to a solution of 50 mg (0.011 mmol) of N-(3-aminophenyl)-N′-[3-methoxy-4-(5-oxazolyl)phenyl]oxalamide trifluoroacetate and 32 mg (0.317 mmol) of triethylamine in 0.5 ml of dimethylformamide. The resulting solution was left at room temperature for 18 hours then diluted with ethyl acetate and washed with 10% citric acid solution, saturated sodium bicarbonate and water. The organic phase was dried over magnesium sulphate, evaporated to dryness and the residue chromatographed on silica gel using ethyl acetate/petrol (1:1) for the elution. There was obtained 5 mg of N-[3-(methanesulphonamido)phenyl]-N′-[3-methoxy-4-(5-oxazolyl)phenyl]oxalamide as a white solid. MS: m/e 431.0 [M+H]+.

Workup

  1. washwashed with 10% citric acid solution, saturated sodium bicarbonate and water
  2. dry with materialThe organic phase was dried over magnesium sulphate
  3. customevaporated to dryness
  4. customthe residue chromatographed on silica gel
  5. washfor the elution

Sources & evidence

ORD record
ord-cf7eb367177c47d693d96f383583bbf8
Source dataset
uspto-grants-2005_03
Patent number
US06867299B2

Reaction notes

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