HCID 21084046, compound → HCID 21084042, compound

HRID 347931Notes

Reaction equation

HRID 347931 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:15](=[O:16])[CH:14]=[CH:13][C:12]2[C:17]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[S:19][C:11]1=2)([O-])=O>[Pd].CCO>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[N:10]1[C:15](=[O:16])[CH:14]=[CH:13][C:12]2[C:17]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[C:18]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[S:19][C:11]1=2

Participants

4

Reactant 1

HCID 21084046HCID 21084046, compound

Product 1

HCID 21084042HCID 21084042, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of the compound of Example 120 (455 mg, 1.08 mmol) and palladium on charcoal (10% Pd wt/wt, 90 mg) in EtOH (20 mL) was stirred under an atmosphere of hydrogen (balloon) for 45 h. The catalyst was filtered off and the filtrate concentrated in vacuo. Purification by column chromatography on silica (3% to 5% THF in DCM) gave the title compound as a pale yellow solid (257 mg, 61%). δH (DMSO-d6) 7.59–7.52 (3H, m), 7.48–7.44 (3H, m), 7.33–7.28 (1H, m), 7.16 (1H, dd, J 1.5, 7.8 Hz), 6.98 (1H, dd, J 1.2, 8.2 Hz), 6.77–6.73 (1H, m), 6.59 (1H, d, J 9.6 Hz), 5.33 (2H, br s), 4.12 (2H, q, J 7.1 Hz), 1.12 (3H, t, J 7.1 Hz). ). LCMS (ES+) RT 3.581 minutes, 391.0 (M+H)+.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated in vacuo
  3. customPurification by column chromatography on silica (3% to 5% THF in DCM)

Sources & evidence

ORD record
ord-2396737d91b14a7fa5acc231aa0c46cc
Source dataset
uspto-grants-2007_02
Patent number
US07176215B2

Reaction notes

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