p-Toluenesulfonic acid monohydrate → HCID 59495694, compound

HRID 219992Notes

Reaction equation

HRID 219992 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.COC1C=C(OC)C=CC=1C[NH:18][C:19](=[O:46])[C:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:30]=[C:29]([C:31]3[CH:36]=[CH:35][C:34]([C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[CH3:43])=[C:33]([CH3:44])[CH:32]=3)[O:28][N:27]=2)=[CH:22][C:21]=1[F:45]>C1(C)C=CC=CC=1>[CH3:44][C:33]1[CH:32]=[C:31]([C:29]2[O:28][N:27]=[C:26]([C:23]3[CH:24]=[CH:25][C:20]([C:19]([NH2:18])=[O:46])=[C:21]([F:45])[CH:22]=3)[N:30]=2)[CH:36]=[CH:35][C:34]=1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[CH3:43]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 67528468HCID 67528468, compound

Product 1

HCID 59495694HCID 59495694, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

Toluene-4-sulfonic acid monohydrate (141.53 mg; 0.74 mmol) was added to a mixture of N-(2,4-dimethoxybenzyl)-4-[5-(2,2′-dimethylbiphenyl-4-yl)-1,2,4-oxadiazol-3-yl]-2-fluorobenzamide, obtained in step 1 and toluene (2 mL). The mixture was heated at 110° C. The reaction was quenched with water (3 mL) and extracted with EtOAc (3×5 mL). The organic layer was then dried over magnesium sulfate, filtered and concentrated. The crude was purified with MD Autoprep, to afford the title compound as a white solid. LC/MS (Method B): 388.3 (M+H)+. HPLC (Method A) Rt 5.20 min (Purity: 100.0%).

Workup

  1. customThe reaction was quenched with water (3 mL)
  2. extractionextracted with EtOAc (3×5 mL)
  3. dry with materialThe organic layer was then dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude was purified with MD Autoprep

Sources & evidence

ORD record
ord-605517c2fb7145a3965fc180a3f3e35d
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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