HCID 86622678, compound → HCID 59783505, compound

HRID 718093Notes

Reaction equation

HRID 718093 reaction equation
C([O:8][N:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:24](=[O:25])[C:23]2[CH2:26][CH2:27][CH:28]=[CH:29][C:22]=2[O:21][C:20]2[CH:30]=[CH:31][CH:32]=[CH:33][C:19]1=2)[CH:10]=[O:11])C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:8][N:9]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][N:18]1[C:24](=[O:25])[C:23]2[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=2[O:21][C:20]2[CH:30]=[CH:31][CH:32]=[CH:33][C:19]1=2)[CH:10]=[O:11]

Participants

5

Reactant 2

HCID 86622678HCID 86622678, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59783505HCID 59783505, compoundYield 6.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Title compound 403 (348 mg, 0.783 mmol) was dissolved in methanol (10 mL). The 10% palladium on charcoal (120 mg, 33% by wt) was added. The reaction mixture was stirred for 3 hours under 1 atmosphere of hydrogen at room temperature. The reaction mixture was filtered to remove the catalyst and the filtrate was evaporated. The residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered and evaporated to afford title compound 404 (18 mg, 6%) as a white solid. 1H NMR (CD3OD) δ (ppm): 8.24, 7.89 (2s, rotamers, 1H), 7.74 (d, J=7.6 Hz, 1H), 7.54-7.46 (m, 2H), 7.33 (dt, J=7.4, 2.0 Hz, 1H), 7.28-7.21 (m, 4H), 4.19 (br s, 2H), 3.50 (t, J=6.8 Hz, 1H), 3.44 (t, J=6.8 Hz, 1H), 1.70-1.55 (m, 4H), 1.44-1.29 (m, 4H). MS (m/z): 355.2 (M+H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove the catalyst
  3. customthe filtrate was evaporated
  4. customThe residue was partitioned between ethyl acetate and water
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-9196118102e44da2b434a3c7b5b745fe
Source dataset
uspto-grants-2015_11
Patent number
US09193749B2

Reaction notes

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