Pyridine → HCID 86620383, compound

HRID 252707Notes

Reaction equation

HRID 252707 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]2[CH:9]=[C:10]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[C:11]([Cl:14])=[N:12][CH:13]=2)=[C:5]([CH3:7])[N:6]=1.N1C=CC=CC=1.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:28]>C1COCC1.CN(C=O)C>[C:30]1([O:29][C:27](=[O:28])[NH:1][C:2]2[S:3][C:4]([C:8]3[CH:13]=[N:12][C:11]([Cl:14])=[C:10]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:9]=3)=[C:5]([CH3:7])[N:6]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 15891Phenyl chloroformate2×HCID 86620384HCID 86620384, compound

Product 1

HCID 86620383HCID 86620383, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

N-[5-(2-Amino-4-methyl-1,3-thiazol-5-yl)-2-chloropyridin-3-yl]methanesulfonamide (63 mg, purity 88%, 0.17 mmol) was dissolved in a mixture of THF (1 mL) and DMF (1 mL) and cooled to 0° C. Pyridine (0.103 mL, 1.27 mmol) was added followed by phenyl chloroformate (0.027 mL, 0.2 mmol). The stirring was continued for 25 minutes at 0° C. and at room temperature for 1 hour. Additional phenyl chloroformate (0.013 mL, 0.1 mmol) was added and the stirring was continued for 45 minutes. The reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate. The organic phase was washed with saturated aqueous sodium hydrogen carbonate, twice with water and finally with brine. Evaporation of the organic solvent at reduced pressure gave N-[5-(6-chloro-5-methanesulfonylaminopyridin-3-yl)-4-methyl-1,3-thiazol-2-yl]carbamic acid phenyl ester which was used without purification; Mass Spectrum: M+H+ 439 and 441.

Workup

  1. waitthe stirring was continued for 45 minutes
  2. customThe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogen carbonate
  3. washThe organic phase was washed with saturated aqueous sodium hydrogen carbonate, twice with water and finally with brine
  4. customEvaporation of the organic solvent at reduced pressure

Sources & evidence

ORD record
ord-0c83dc2a23134d6a9beb4affb6d0aa4f
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

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