Methanesulfonyl chloride → HCID 58941889, compound

HRID 1845773Notes

Reaction equation

HRID 1845773 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[O:12][N:11]=[C:10]2[C:15]2[N:16]=[N:17][S:18][C:19]=2[CH2:20][OH:21])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:22][S:23](Cl)(=[O:25])=[O:24]>C(Cl)Cl>[CH3:22][S:23]([O:21][CH2:20][C:19]1[S:18][N:17]=[N:16][C:15]=1[C:10]1[N:9]([C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=2)[C:13](=[O:14])[O:12][N:11]=1)(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 58941884HCID 58941884, compound

Product 1

HCID 58941889HCID 58941889, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

4-(3-Chloro-4-fluorophenyl)-3-[5-(hydroxymethyl)-1,2,3-thiadiazol-4-yl]-1,2,4-oxadiazol-5(4H)-one was dissolved in anhydrous DCM (2 mL) followed by addition of TEA (26 μL, 0.19 mmol). The reaction was stirred at 0° C. for 15 minutes. Methanesulfonyl chloride (13 μL, 0.17 mmol) was added drop-wise and stirred for 15 minutes at 0° C. The reaction was concentrated in vacuo and the crude purified by flash chromatography to give the desired product (42 mg, 65%). 1H NMR (400 MHz, CDCl3): δ 7.50 (m, 1H), 7.25 (m, 2H), 5.83 (s, 2H), 3.20 (s, 3H). MF C12H8ClFN4O5S2; LCMS calculated for C12H9ClFN4O5S2(M+H)+: m/z=406.9.

Workup

  1. stirringstirred for 15 minutes at 0° C
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe crude purified by flash chromatography

Sources & evidence

ORD record
ord-be519f33a4dc485e960fdeb23f485f2a
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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