HCID 9947985, compound → HCID 9882561, compound

HRID 2085368Notes

Reaction equation

HRID 2085368 reaction equation
[C:1]([C:5]1[O:9][C:8](/[CH:10]=[CH:11]/[C:12]2[S:16][C:15]([NH:17][C:18](=[O:20])[CH3:19])=[N:14][CH:13]=2)=[N:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([C:5]1[O:9][C:8]([CH2:10][CH2:11][C:12]2[S:16][C:15]([NH:17][C:18](=[O:20])[CH3:19])=[N:14][CH:13]=2)=[N:7][CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 9947985HCID 9947985, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 9882561HCID 9882561, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution N-[(E)-5-(2-(5-t-butyl-oxazol-2-yl)-vinyl)-thiazol-2-yl]acetamide (67 mg, 0.23 mmol) in ethyl acetate (10 mL) was added to a suspension of pre-reduced Pd/C (10%) in ethyl acetate (5 mL). The reaction flask was fitted with a hydrogen balloon and stirred for 24 hours. The reaction was filtered, and the mixture was resubmitted to hydrogenation using the same conditions as above. After an additional 24 hours, the reaction was filtered through a plug of celite, concentrated, and purified by chromatography (SiO2, 5% MeOH/CHCl3) to give N-[5-(2-(5-t-butyl-oxazol-2-yl)-ethyl)-thiazol-2-yl]-acetamide as a white solid (3.5 mg, 5%, C14H19N3O2S, MS m/e 294 (M+H)+). HPLC-HI 91% at 6.75 min (Zorbax SB C18 column 4.6×75 mm, 10-90% aqueous methanol over 8 minutes containing 0.1% TFA, 2.5 mL/min, monitoring at 220 nm).

Workup

  1. filtrationThe reaction was filtered
  2. waitAfter an additional 24 hours
  3. filtrationthe reaction was filtered through a plug of celite,
  4. concentrationconcentrated
  5. custompurified by chromatography (SiO2, 5% MeOH/CHCl3)

Sources & evidence

ORD record
ord-c23ae320822f4b7d9c3141bd4962f133
Source dataset
uspto-grants-2004_04
Patent number
US06720347B2

Reaction notes

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