Acetic Acid → HCID 59303062, compound

HRID 1692140Notes

Reaction equation

HRID 1692140 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[C:19]([F:21])[C:18]([Cl:22])=[CH:17][C:16]=2[C:23]2O[C:25]([CH2:28][CH2:29][S:30]([CH3:33])(=[O:32])=[O:31])=[N:26][N:27]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:34][NH2:35].CC(O)=O>O1CCOCC1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[C:19]([F:21])[C:18]([Cl:22])=[CH:17][C:16]=2[C:23]2[N:35]([CH3:34])[C:25]([CH2:28][CH2:29][S:30]([CH3:33])(=[O:32])=[O:31])=[N:26][N:27]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6329MethylamineHCID 59303083HCID 59303083, compound

Product 1

HCID 59303062HCID 59303062, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A 25 mL scintillation vial was charged with 4-tert-butyl-N-{4-chloro-5-fluoro-2-[5-(2-methanesulfonyl-ethyl)-[1,3,4]oxadiazol-2-yl]-phenyl}-benzenesulfonamide (48 mg, 0.093 mmol), methylamine (13 μL, 0.372 mmol), AcOH (21 μL, 0.372 mmol), and dioxane (1.0 mL). The vial was sealed, heated to 120° C., and stirred overnight. The following day, the volatiles were evacuated in vacuo and the residue was purified via automated silica gel chromatography to afford 4-tert-butyl-N-{4-chloro-5-fluoro-2-[5-(2-methanesulfonyl-ethyl)-4-methyl-4H-[1,2,4]triazol-3-yl]-phenyl}-benzenesulfonamide as a white powder: MS (ES) M+H expected 529.1, found 529.0.

Workup

  1. customThe vial was sealed
  2. customThe following day, the volatiles were evacuated in vacuo
  3. customthe residue was purified

Sources & evidence

ORD record
ord-c7ac04dffbff4f97b51ab3074e3b98e9
Source dataset
uspto-grants-2012_04
Patent number
US08153818B2

Reaction notes

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