Hydrochloric Acid → HCID 58941884, compound

HRID 1845772Notes

Reaction equation

HRID 1845772 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][O:21][Si](C(C)C)(C(C)C)C(C)C)[CH:5]=[CH:6][C:7]=1[F:8].CO.Cl>O1CCOCC1>[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]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 58941918HCID 58941918, compound

Product 1

HCID 58941884HCID 58941884, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

Into a round bottom flask was added 4-(3-chloro-4-fluorophenyl)-3-(5-[(triisopropylsilyl)-oxy]methyl-1,2,3-thiadiazol-4-yl)-1,2,4-oxadiazol-5(4H)-one (89 mg, 0.18 mmol), anhydrous MeOH (1.5 mL), and hydrogen chloride in 1,4-dioxane (1.5 mL, 4.0 M). The reaction was heated to 70° C. for 2.5 h. The reaction was concentrated in vacuo and the crude purified by flash chromatography to give the desired product (52 mg, 86%). MF=C11H6ClFN4O3S; LCMS calculated for C11H7ClFN4O3S (M+H)+: m/z=329.0.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. customthe crude purified by flash chromatography

Sources & evidence

ORD record
ord-e6f09e8c239f48b5a500779217244c3a
Source dataset
uspto-grants-2015_02
Patent number
US08951536B2

Reaction notes

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