Methanesulfonamide → HCID 66633773, compound

HRID 2359927Notes

Reaction equation

HRID 2359927 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][C:10]([C:14]3[CH:18]=[C:17]([C:19](O)=[O:20])[N:16]([CH3:22])[N:15]=3)=[C:11]([CH3:13])[N:12]=2)[CH:5]=[N:6][CH:7]=1.[CH3:23][S:24]([NH2:27])(=[O:26])=[O:25].Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.ClCCl>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[S:9][C:10]([C:14]3[CH:18]=[C:17]([C:19]([NH:27][S:24]([CH3:23])(=[O:26])=[O:25])=[O:20])[N:16]([CH3:22])[N:15]=3)=[C:11]([CH3:13])[N:12]=2)[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 72879MethanesulfonamideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 66633628HCID 66633628, compound

Product 1

HCID 66633773HCID 66633773, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-[2-(5-Fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-1-methyl-1H-pyrazole-5-carboxylic acid (0.08 g, 0.25 mmol) and methanesulphonamide (0.024 g, 0.25 mmol) were initially charged in ice-cooled dichloromethane (10 ml). 4-Dimethylaminopyridine (0.006 g, 0.05 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (0.053 g, 0.275 mmol) were added. The reaction mixture was stirred at 0° C. for 2 h and then at room temperature for 16 h. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel (dichloromethane/ethyl acetate eluent). This gave 0.074 g (72% of theory) of 3-[2-(5-fluoropyridin-3-yl)-4-methyl-1,3-thiazol-5-yl]-1-methyl-N-(methylsulphonyl)-1H-pyrazole-5-carboxamide.

Workup

  1. waitat room temperature for 16 h
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was chromatographed on silica gel (dichloromethane/ethyl acetate eluent)

Sources & evidence

ORD record
ord-9b5e15f170ef409daf223e7b9e74728e
Source dataset
uspto-grants-2014_04
Patent number
US08686004B2

Reaction notes

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