HCID 59313790, compound → HCID 59313983, compound

HRID 889444Notes

Reaction equation

HRID 889444 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:12]([S:17]([CH3:20])(=[O:19])=[O:18])[S:13]([CH3:16])(=[O:15])=[O:14])[CH:6]=[C:7]([N+:9]([O-])=O)[CH:8]=1)#[N:2]>CO.CCOC(C)=O.[Pd]>[NH2:9][C:7]1[CH:6]=[C:5]([N:12]([S:13]([CH3:16])(=[O:15])=[O:14])[S:17]([CH3:20])(=[O:18])=[O:19])[CH:4]=[C:3]([C:1]#[N:2])[CH:8]=1

Participants

5

Reactant 1

HCID 59313790HCID 59313790, compound

Product 1

HCID 59313983HCID 59313983, compoundYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of Intermediate 76A (240 mg, 0.752 mmol) and 10% Pd/C (105 mg, 0.099 mmol) in MeOH (30 mL) and EtOAc (15 mL) was degassed and then stirred under a hydrogen atmosphere (balloon) for 1.5 hours. The catalyst was filtered off, and the filtrate was concentrated to give Intermediate 76 (215 mg, 99%). HPLC: Rt=0.847 min. (CHROMOLITH® column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 min. containing 0.1% TFA, 4 mL/min., monitoring at 220 nm). 1H NMR (400 MHz, DMSO-d6) δ ppm 8.93 (1H, s), 8.82 (1H, d, J=1.76 Hz), 7.43 (1H, t, J=1.63 Hz), 7.23 (1H, s), 7.14 (1H, t, J=2.01 Hz), 3.55 (6H, s). Intermediate 76 was used in the synthesis of Example 179.

Workup

  1. customwas degassed
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-41f875815c224c16a573503d921a6085
Source dataset
uspto-grants-2012_08
Patent number
US08252795B2

Reaction notes

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