HCID 86649986, compound → HCID 86649987, compound

HRID 1892479Notes

Reaction equation

HRID 1892479 reaction equation
[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH:10]=[CH:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[C:14]([F:21])[CH:13]=2)[N:9]=1)(=[O:3])[CH3:2]>O1CCCC1.CO.C(O)(=O)C.[C].[Pd]>[C:1]([NH:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][CH2:11][C:12]2[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[C:14]([F:21])[CH:13]=2)[N:9]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 1

HCID 86649986HCID 86649986, compound

Product 1

HCID 86649987HCID 86649987, compoundYield 77.5%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixed solution of 4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]vinyl}-2-fluorobenzoic acid (738.9 mg, 2.412 mmol) in tetrahydrofuran (105 ml), methanol (105 ml) and acetic acid (21 ml) was added 10% palladium carbon (593.0 mg, containing 50% water), and the mixture was hydrogenated at room temperature and atmospheric pressure. The reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure. The resulting solid was collected by filtration, washed with diisopropyl ether, and dried under reduced pressure to give 4-{2-[2-(acetylamino)-1,3-thiazol-4-yl]ethyl}-2-fluorobenzoic acid (576.2 mg, 1.869 mmol, yield 77.5%) as a white solid.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with diisopropyl ether
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-768a7437609b48f49316e74ecec8750e
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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