1,4-Cyclohexadiene → HCID 9867344, compound

HRID 585414Notes

Reaction equation

HRID 585414 reaction equation
C([O:8][C:9](=[O:39])[CH2:10][O:11][C:12]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH:18]=[C:17]2[C:13]=1[C:14]([C:34](=[O:38])[C:35]([NH2:37])=[O:36])=[C:15]([CH2:32][CH3:33])[N:16]2[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)C1C=CC=CC=1.C1CC=CCC=1>O1CCCC1.[Pd]>[NH2:37][C:35](=[O:36])[C:34]([C:14]1[C:13]2[C:17](=[CH:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:12]=2[O:11][CH2:10][C:9]([OH:39])=[O:8])[N:16]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:15]=1[CH2:32][CH3:33])=[O:38]

Participants

5

Reactant 2

HCID 123431,4-CyclohexadieneHCID 10229780HCID 10229780, compound

Product 1

HCID 9867344HCID 9867344, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-[[3-(2-amino-1,2-dioxoethyl)-1-benzyl-2-ethyl-1H-benz[f]indol-4-yl]oxy]acetic acid benzyl ester (29 mg, 0.056 mmol), 10% palladium-on-carbon (30 mg), and 1,4-cyclohexadiene (1 mL) in tetrahydrofuran (1 mL) was warmed to 50° C. with stirring for 3 h. The mixture was filtered and the resulting solution concentrated in vacuo. The filtered solids were washed with methanol and the resulting solution concentrated in vacuo. Both residues were dissolved methylene chloride and diluted with hexane. The resulting precipitate was collected via vacuum filtration to provide 8.8 mg (37%) of the title compound as a solid: mp 243-253° C. (dec). 1H NMR (DMSO-d6) δ8.26 (m, 1H), 8.11 (bs, 1H), 7.89 (m, 1H), 7.75 (s, 1H), 7.53 (s, 1H), 7.34 (m, 2H), 7.30 (m, 2H), 7.22 (t, J=7.0 Hz, 1H), 7.07 (d, J=7.3 Hz, 2H), 5.60 (s, 2H), 4.47 (s, 2H), 2.97 (q, J=7.7 Hz, 2H), 1.10 (t, J=7.3 Hz, 3H); TOF MS ES+ exact mass calculated for C25H23N2O5: m/z=431.1607 (p+1). Found: 431.1605.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe resulting solution concentrated in vacuo
  3. washThe filtered solids were washed with methanol
  4. concentrationthe resulting solution concentrated in vacuo
  5. dissolutionBoth residues were dissolved methylene chloride
  6. additiondiluted with hexane
  7. filtrationThe resulting precipitate was collected via vacuum filtration

Sources & evidence

ORD record
ord-8fbd37dae75d4260bf00b386d25d9050
Source dataset
uspto-grants-2005_08
Patent number
US06930123B2

Reaction notes

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