Pyridine → HCID 86662770, compound

HRID 2359726Notes

Reaction equation

HRID 2359726 reaction equation
[F:1][CH:2]([F:23])[CH2:3][N:4]1[C:9]2[N:10]=[CH:11][S:12][C:8]=2[C:7]([OH:13])=[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[I:20])[S:5]1(=[O:22])=[O:21].N1C=CC=C[CH:25]=1.Cl[C:31]([O:33]C)=[S:32]>ClCCl>[C:31](=[O:32])([S:33][CH3:25])[O:13][C:7]1[C:8]2[S:12][CH:11]=[N:10][C:9]=2[N:4]([CH2:3][CH:2]([F:1])[F:23])[S:5](=[O:21])(=[O:22])[C:6]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[I:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 554404Methyl chloromethanethioateHCID 86662768HCID 86662768, compound

Product 1

HCID 86662770HCID 86662770, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

150 mg (0.3 mmol) of 1-(2,2-difluoroethyl)-3-(2-iodophenyl)-1H-[1,3]thiazolo[4,5-c][1,2]thiazin-4-ol 2,2-dioxide (compound I-a-14) were dissolved in 5 ml of dichloromethane, and 0.04 ml (0.48 mmol) of pyridine was added at RT. The reaction mixture was stirred at RT for 5 min, and then 0.03 ml (0.38 mmol) of methyl chlorothioformate was added and the mixture was stirred at RT for a further 4 h. After removing the solvent under reduced pressure, the residue was purified by column chromatography (SiO2, gradient ethyl acetate/n-heptane 10:90 to 75:25). This gave 144 mg of compound I-c-16.

Workup

  1. stirringthe mixture was stirred at RT for a further 4 h
  2. customAfter removing the solvent under reduced pressure
  3. customthe residue was purified by column chromatography (SiO2, gradient ethyl acetate/n-heptane 10:90 to 75:25)

Sources & evidence

ORD record
ord-ae3cd20b349c4e6db40558aa95d1e16d
Source dataset
uspto-grants-2014_04
Patent number
US08686000B2

Reaction notes

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