p-Toluenesulfonic acid → HCID 178486444, compound

HRID 62257Notes

Reaction equation

HRID 62257 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][C:9]2=[O:12])=[CH:5][C:4]=1[N:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.[CH3:19][C:20]1[CH:24]=[C:23]([CH:25]=O)[NH:22][N:21]=1.CC1C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7]/[C:8](=[CH:25]\[C:23]3[NH:22][N:21]=[C:20]([CH3:19])[CH:24]=3)/[C:9]2=[O:12])=[CH:5][C:4]=1[N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 1179401286-Methoxy-5-morpholino-2,3-dihydro-1H-inden-1-oneHCID 178427211HCID 178427211, compound

Product 1

HCID 178486444HCID 178486444, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 13 (100 mg, 0.404 mmol) in toluene 10 mL was added 3-methyl-1H-pyrazole-5-carbaldehyde 93 (70.8 mg, 0.404 mmol). PTSA (153.8 mg, 0.808 mmol) was added to the reaction mass, then stirred at 120° C. for 6 h, diluted with ethyl acetate and washed with water (3×25 mL). The organic layer was dried over sodium sulphate and concentrated to get the crude 94 and was purified through flash chromatography by using 100-200 mesh silica gel eluting at 2% MeOH in DCM to afford yellow coloured solid compound (E)-6-methoxy-2-((3-methyl-1H-pyrazol-5-yl)methylene)-5-morpholino-2, 3-dihydro-1H-inden-1-one 94.

Workup

  1. washwashed with water (3×25 mL)
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. concentrationconcentrated
  4. customto get the crude 94
  5. customwas purified through flash chromatography

Sources & evidence

ORD record
ord-65876cc90a1f43ca8dcca6c2507984b4
Source dataset
uspto-grants-2016_09
Patent number
US09446047B2

Reaction notes

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