Propionyl chloride → HCID 91325177, compound

HRID 1800614Notes

Reaction equation

HRID 1800614 reaction equation
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[N:20]=[C:19]3[S:21][C:22]([NH2:24])=[N:23][C:18]3=[CH:17][CH:16]=2)[C:11]([Cl:25])=[CH:10][C:9]=1[F:26])([CH3:4])([CH3:3])[CH3:2].[C:28](Cl)(=[O:31])[CH2:29][CH3:30].C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[C:12]([O:14][C:15]2[N:20]=[C:19]3[S:21][C:22]([NH:24][C:28](=[O:31])[CH2:29][CH3:30])=[N:23][C:18]3=[CH:17][CH:16]=2)[C:11]([Cl:25])=[CH:10][C:9]=1[F:26])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 62324Propionyl chlorideHCID 516892Sodium BicarbonateHCID 91227255Tert-butyl{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-chloro-2-fluorophenyl}carbamate

Product 1

HCID 91325177HCID 91325177, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of tert-butyl{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-chloro-2-fluorophenyl}carbamate (1.30 g, 3.16 mmol) in pyridine (20 mL) was added propionyl chloride (330 μL, 3.80 mmol), and the mixture was stirred at room temperature for 4.5 hr. To the reaction mixture was added aqueous sodium hydrogen carbonate solution (30 mL), and the mixture was extracted with ethyl acetate (50 mL×3). The organic layer was washed successively with water (20 mL) and saturated brine (20 mL), dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→34/66) to give the title compound (1.30 g, 88%) as white crystals.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (50 mL×3)
  2. washThe organic layer was washed successively with water (20 mL) and saturated brine (20 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10→34/66)

Sources & evidence

ORD record
ord-e8dcd78de709490bb90d7f0335515879
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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