HCID 118021500, compound → HCID 118021508, compound

HRID 575839Notes

Reaction equation

HRID 575839 reaction equation
[CH2:1]([C:3]1[O:4][C:5]2[C:11]([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15](=[O:22])[N:14]([CH3:23])[CH:13]=3)=[CH:10][C:9]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:8][C:6]=2[CH:7]=1)[CH3:2]>CO.[Pd]>[CH2:1]([CH:3]1[CH2:7][C:6]2[CH:8]=[C:9]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:10]=[C:11]([C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:15](=[O:22])[N:14]([CH3:23])[CH:13]=3)[C:5]=2[O:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 118021500HCID 118021500, compound

Product 1

HCID 118021508HCID 118021508, compoundYield 9.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of the title compound from Step 2 (130 mg, 340 umol) in MeOH (3 mL) was added Pd/C (70 mg, 10% w/w) in one portion. The reaction mixture was stirred at 25° C. under H2 atmosphere (15 psi) for 8 h. After this time, the mixture was filtered through celite. The solvent was removed under reduced pressure and the residue was purified by prep-HPLC to give the title compound (12.4 mg) as a gray solid. 1H NMR (CDCl3, 300 MHz) δ 8.54-8.51 (d, J=7.5 Hz, 1H), 7.79-7.75 (m, 2H), 7.75-7.54 (m, 2H), 7.32-7.29 (d, J=8.1 Hz, 1H), 7.16 (s, 1H), 4.90-4.85 (m, 1H), 3.69 (s, 3H), 3.49-3.41 (m, 1H), 3.06-3.00 (m, 1H), 1.85-1.70 (m, 2H), 0.96-0.91 (t, J=7.5 Hz, 3H). LCMS: 384.0 (M+1)

Workup

  1. filtrationAfter this time, the mixture was filtered through celite
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was purified by prep-HPLC

Sources & evidence

ORD record
ord-5d519a45bb83427eb1b5eba4dbbabd84
Source dataset
uspto-grants-2015_05
Patent number
US09034900B2

Reaction notes

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