Ammonium Chloride → HCID 86649996, compound

HRID 1892484Notes

Reaction equation

HRID 1892484 reaction equation
[BH4-].[Na+].[F:3][C:4]1[C:9]([F:10])=[C:8]([C:11](N2C=CN=C2)=[O:12])[CH:7]=[CH:6][C:5]=1[CH2:18][CH2:19][C:20]1[N:21]=[C:22]([NH:25][C:26](=[O:28])[CH3:27])[S:23][CH:24]=1.[Cl-].[NH4+]>O1CCCC1.O>[F:3][C:4]1[C:9]([F:10])=[C:8]([CH2:11][OH:12])[CH:7]=[CH:6][C:5]=1[CH2:18][CH2:19][C:20]1[N:21]=[C:22]([NH:25][C:26](=[O:28])[CH3:27])[S:23][CH:24]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 86649994HCID 86649994, compound

Product 1

HCID 86649996HCID 86649996, compoundYield 75.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

Sodium borohydride (1.009 g, 26.66 mmol) was suspended in a mixture of tetrahydrofuran (36 ml) and water (9 ml), and the suspension was cooled to −20° C. A suspension of N-(4-{2-[2,3-difluoro-4-(1H-imidazol-1-ylcarbonyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (503.5 mg, 1.338 mmol) in anhydrous tetrahydrofuran (4 ml) was added dropwise. After stirring at not more than 0° C. for 2.5 hr, saturated aqueous ammonium chloride (50 ml) was added. The mixture was extracted 3 times with ethyl acetate, and the combined organic layer was washed with saturated aqueous ammonium chloride and saturated brine. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. To the residue were added methanol (0.5 ml) and diisopropyl ether (25 ml), and the mixture was stirred and filtered. The filtered product was dried under reduced pressure to give N-(4-{2-[2,3-difluoro-4-(hydroxymethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (316.8 mg, 1.014 mmol, 75.8%) as a white solid.

Workup

  1. additionwas added dropwise
  2. extractionThe mixture was extracted 3 times with ethyl acetate
  3. washthe combined organic layer was washed with saturated aqueous ammonium chloride and saturated brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the residue were added methanol (0.5 ml) and diisopropyl ether (25 ml)
  7. stirringthe mixture was stirred
  8. filtrationfiltered
  9. customThe filtered product was dried under reduced pressure

Sources & evidence

ORD record
ord-eb7c5ed711d74499ad056e399eee6887
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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