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

HRID 1892521Notes

Reaction equation

HRID 1892521 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:12]=[C:13]([NH:16][C:17](=[O:19])[CH3:18])[S:14][CH:15]=2)=[CH:5][C:4]=1[F:20].[N-:21]=[N+:22]=[N-:23].[Na+].O.C(OCC)(=O)C>CN(C)C=O>[N:21]([CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:12]=[C:13]([NH:16][C:17](=[O:19])[CH3:18])[S:14][CH:15]=2)=[CH:5][C:4]=1[F:20])=[N+:22]=[N-:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 86650021N-(4-{2-[4-(chloromethyl)-3-fluorophenyl]ethyl}-1,3-thiazol-2-yl)acetamide

Product 1

HCID 86650022N-(4-{2-[4-(azidomethyl)-3-fluorophenyl]ethyl}-1,3-thiazol-2-yl)acetamideYield 77.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-(4-{2-[4-(chloromethyl)-3-fluorophenyl]ethyl}-1,3-thiazol-2-yl)acetamide (203.3 mg, 0.650 mmol) in anhydrous N,N-dimethylformamide (2 ml) was added sodium azide (233.7 mg, 3.595 mmol), and the mixture was stirred at room temperature for 3.5 hr. Water (20 ml) and ethyl acetate (20 ml) were added to the reaction mixture, and the mixture was stirred, stood still and then partitioned. The aqueous layer was extracted with ethyl acetate, and the combined organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Diisopropyl ether (10 ml) was added to the residue, and the mixture was filtered and dried under reduced pressure to give N-(4-{2-[4-(azidomethyl)-3-fluorophenyl]ethyl}-1,3-thiazol-2-yl)acetamide (160.5 mg, 0.503 mmol, yield 77.3%) as a white solid.

Workup

  1. stirringthe mixture was stirred
  2. custompartitioned
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washthe combined organic layer was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionDiisopropyl ether (10 ml) was added to the residue
  8. filtrationthe mixture was filtered
  9. customdried under reduced pressure

Sources & evidence

ORD record
ord-b9f7383c3708451d872254fb7ac856db
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

Loading…