HCID 10204560, compound → HCID 18189043, compound

HRID 1358144Notes

Reaction equation

HRID 1358144 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]1[CH:26]=[CH:25][C:24]([NH:27][S:28]([CH3:31])(=[O:30])=[O:29])=[CH:23][C:6]=1[CH:7]([C:13]1[S:14][C:15]([C:18]#[C:19][CH2:20][O:21][CH3:22])=[CH:16][CH:17]=1)[O:8]2>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]1[CH:26]=[CH:25][C:24]([NH:27][S:28]([CH3:31])(=[O:29])=[O:30])=[CH:23][C:6]=1[CH:7]([C:13]1[S:14][C:15]([CH2:18][CH2:19][CH2:20][O:21][CH3:22])=[CH:16][CH:17]=1)[O:8]2

Participants

4

Reactant 1

HCID 10204560HCID 10204560, compound

Product 1

HCID 18189043HCID 18189043, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

A solution of Example 92 (0.05 g, 0.11 mmol) was treated with 10% Pd/C (0.011 g) in MeOH (2 mL) under an atmosphere of hydrogen (50 psi) for 1.5 hour, followed by 10% Pd/C (0.012 g) under an atmosphere of hydrogen 50 psi for 3 hours. The mixture was filtered and concentrated under reduced pressure to afford the titled compound (38 mg, 0.08 mmol, 75%). 1H NMR (500 MHz, CD3OD) δ 8.41 (d, J=8.7 Hz, 1H), 7.25 (dd, J=8.7, 2.5 Hz, 1 H), 7.11 (t, J=8.3 Hz, 1H), 7.05 (d, J=2.2 Hz, 1H), 6.69 (dd, J=8.4, 0.9 Hz, 1H), 6.61 (dd, J=3.4, 0.9 Hz, 1H), 6.57 (m, 2H), 6.25 (s, 1H), 3.92 (s, 3H), 3.35 (t, J=6.2 Hz, 2H), 3.28 (s, 3H), 2.96 (s, 3H), 2.77 (t, J=7.5 Hz, 2H), 1.81 (m, 2H); MS (ESI, −Q1MS) m/e 460 (M−H).

Workup

  1. customfor 3 hours
  2. filtrationThe mixture was filtered
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-59cf94ab24974fc9bb6ed11003522318
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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