HCID 178526836, compound → HCID 178508039, compound

HRID 2375899Notes

Reaction equation

HRID 2375899 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:11]2[S:15][CH:14]=[N:13][CH:12]=2)[C:7]([OH:10])=[N:8][CH:9]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:11]2[S:15][CH:14]=[N:13][CH:12]=2)[C:7]([OH:10])=[N:8][CH:9]=1

Participants

4

Reactant 1

HCID 178526836HCID 178526836, compound

Product 1

HCID 178508039HCID 178508039, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-nitro-3-thiazol-5-ylpyridin-2-ol (218 mg, 0.977 mmol) and 10% Pd/C (100 mg) in methanol (5 mL) was hydrogenated under 1 atm at rt for 5 h. The resulting mixture was filtered through a Celite pad. The filtrate was concentrated under reduced pressure to give 170 mg of the title compound, which was used directly in the next step without purification. 1H-NMR (DMSO-d6, 400 MHz): δ=4.38 (s, br, 2H), 6.78 (d, J=2.8 Hz, 1H), 7.80 (d, J=2.8 Hz, 1H), 8.41 (s, 1H), 8.97 (s, 1H), 11.52 (s, br, 1H). MS (ES+): m/z 194.15 [MH+]. HPLC: tR=0.49 and 0.90 min (ZQ2000, polar—5 min).

Workup

  1. filtrationThe resulting mixture was filtered through a Celite pad
  2. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e50beed92ae040dca498aaf9e8720376
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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