HCID 24740194, compound → HCID 24740195, compound

HRID 273353Notes

Reaction equation

HRID 273353 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:42]([O:44][CH3:45])=[O:43])=[CH:12][C:13]=3[N:14]3[CH2:20][C:19]([C:21]4[O:22][C:23]([CH2:26][CH2:27][C:28]([N:30]5[CH2:35][CH2:34][O:33][CH2:32][CH2:31]5)=[O:29])=[CH:24][N:25]=4)=[CH:18][C:17]4[CH:36]=[C:37]([O:40][CH3:41])[CH:38]=[CH:39][C:16]=4[C:15]=23)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1>C1COCC1.CO.[Pd]>[CH:1]1([C:7]2[C:8]3[CH:9]=[CH:10][C:11]([C:42]([O:44][CH3:45])=[O:43])=[CH:12][C:13]=3[N:14]3[CH2:20][CH:19]([C:21]4[O:22][C:23]([CH2:26][CH2:27][C:28]([N:30]5[CH2:31][CH2:32][O:33][CH2:34][CH2:35]5)=[O:29])=[CH:24][N:25]=4)[CH2:18][C:17]4[CH:36]=[C:37]([O:40][CH3:41])[CH:38]=[CH:39][C:16]=4[C:15]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 1

HCID 24740194HCID 24740194, compound

Product 1

HCID 24740195HCID 24740195, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Methyl 13-cyclohexyl-3-methoxy-6-(5-(3-(4-morpholinyl)-3-oxopropyl)-1,3-oxazol-2-yl)-7H-indolo[2,1-a][2]benzazepine-10-carboxylate (610 mg, 1.00 mMol)) was dissolved in 15 ml of THF and 5 ml of methanol. To this reaction was added 83 mg of 10% palladium on carbon. The reaction was placed under hydrogen atmosphere (1 atm, balloon pressure) and stirred at room temperature for 22 hrs. The reaction was filtered through a celite plug and rinsed with THF. Volatiles were removed from the filtrate in vacuuo to yield 569 mg (93%) of the title compound as a yellow solid. LC-MS: Shimadzu Analytical HPLC using Discovery VP software: % A=10% methanol, 90% water, 0.1% trifluoroacetic acid; % B=90% methanol, 10% water, 0.1% trifluoroacetic acid; Initial % B=50; Final % B=100; Gradient=3 min; Runtime=4 min; Flow rate=5 ml/min; Wavelength=220 nm; Column=Phenomenex Luna 3.0 mm×50 mm S10. Retention Time=2.55 min, MS m/z 612(MH+).

Workup

  1. filtrationThe reaction was filtered through a celite plug
  2. washrinsed with THF
  3. customVolatiles were removed from the filtrate in vacuuo

Sources & evidence

ORD record
ord-d3d13af4d659461fb48d2727b18577fc
Source dataset
uspto-grants-2008_11
Patent number
US07456165B2

Reaction notes

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