Methanesulfonamide → HCID 57651949, compound

HRID 1691926Notes

Reaction equation

HRID 1691926 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]([C:20]2[N:21]=[C:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:23][C:24]=2[C:25]([F:28])([F:27])[F:26])=[O:19])=[CH:13][N:12]=1)[C:5]([OH:7])=O.[CH3:35][S:36]([NH2:39])(=[O:38])=[O:37].Cl.C(N=C=NCCCN(C)C)C>CN(C)C1C=CN=CC=1.ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]([NH:39][S:36]([CH3:35])(=[O:38])=[O:37])=[O:7])[CH:8]=[CH:9][C:10]=1[C:11]1[N:12]=[CH:13][C:14]([NH:17][C:18]([C:20]2[N:21]=[C:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:23][C:24]=2[C:25]([F:27])([F:28])[F:26])=[O:19])=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57652100HCID 57652100, compound

Product 1

HCID 57651949HCID 57651949, compoundYield 35.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

According to the procedures described in Tetrahedron Lett. 1998, 39, 5891 and Org. Proc. Res. Dev. 2004, 8, 952, 3-chloro-4-{5-[(2-phenyl-5-trifluoromethyl-oxazole-4-carbonyl)-amino]-pyridin-2-yl}-benzoic acid (30 mg, 0.06 mmol), methanesulfonamide (7 mg, 0.07 mmol), 4-dimethylaminopyridine (2 mg, 0.02 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (14 mg, 0.07 mmol) were suspended in 3 mL of dichloromethane and the mixture was refluxed for 3 h. The reaction mixture was cooled down to room temperature and filtered. The white precipitates were washed with ethyl acetate. The combined filtrate was stirred with 150 mg of Amberlyst-15 at room temperature for 2 h. The reaction was filtered to remove the resin, and the filtrate was concentrated and purified by flash chromatography (eluting with ethyl acetate and hexanes) to afford 12 mg of 2-phenyl-5-trifluoromethyl-oxazole-4-carboxylic acid [6-(2-chloro-4-methanesulfonylaminocarbonyl-phenyl)-pyridin-3-yl]-amide as a light yellow solid. LCMS calcd for C24H16ClF3N4O5S (m/e) 564, obsd 565 (M+H).

Workup

  1. temperaturethe mixture was refluxed for 3 h
  2. filtrationfiltered
  3. customThe white precipitates
  4. washwere washed with ethyl acetate
  5. filtrationThe reaction was filtered
  6. customto remove the resin
  7. concentrationthe filtrate was concentrated
  8. custompurified by flash chromatography (eluting with ethyl acetate and hexanes)

Sources & evidence

ORD record
ord-ef92564a526d45339b95c997fc3beaf1
Source dataset
uspto-grants-2012_04
Patent number
US08153644B2

Reaction notes

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