Methanol → N-(4-{2-[4-(aminomethyl)-3-fluorophenyl]ethyl}-1,3-thiazol-2-yl)acetamide

HRID 1892522Notes

Reaction equation

HRID 1892522 reaction equation
[N:1]([CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]2[N:14]=[C:15]([NH:18][C:19](=[O:21])[CH3:20])[S:16][CH:17]=2)=[CH:7][C:6]=1[F:22])=[N+]=[N-].CO>C(OCC)(=O)C.[C].[Pd]>[NH2:1][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][C:13]2[N:14]=[C:15]([NH:18][C:19](=[O:21])[CH3:20])[S:16][CH:17]=2)=[CH:7][C:6]=1[F:22]

Participants

5

Reactant 2

HCID 887MethanolHCID 86650022N-(4-{2-[4-(azidomethyl)-3-fluorophenyl]ethyl}-1,3-thiazol-2-yl)acetamide

Product 1

HCID 86650023N-(4-{2-[4-(aminomethyl)-3-fluorophenyl]ethyl}-1,3-thiazol-2-yl)acetamideYield 85.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of N-(4-{2-[4-(azidomethyl)-3-fluorophenyl]ethyl}-1,3-thiazol-2-yl)acetamide (152.3 mg, 0.477 mmol) in ethyl acetate (21 ml) was added 10% palladium carbon (30.5 mg, containing 50% water), and the mixture was hydrogenated at room temperature under an atmospheric pressure. Ethyl acetate (5 ml) and methanol (5 ml) were added to the reaction mixture, and the mixture was filtered through celite. The filtrate was concentrated under reduced pressure, and the resulting solid was collected by filtration, washed with tert-butyl methyl ether (5 ml) and dried under reduced pressure to give N-(4-{2-[4-(aminomethyl)-3-fluorophenyl]ethyl}-1,3-thiazol-2-yl)acetamide (119.3 mg, 0.407 mmol, yield 85.3%) as a white solid.

Workup

  1. customwas hydrogenated at room temperature under an atmospheric pressure
  2. filtrationthe mixture was filtered through celite
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. filtrationthe resulting solid was collected by filtration
  5. washwashed with tert-butyl methyl ether (5 ml)
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-2c25d360d6124fd59c9e87daa2f1fa31
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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