Acetyl chloride → N-(5-{[2-(acetylamino) [1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-4-chloro-2-fluorophenyl)-2,2,2-trifluoroacetamide

HRID 1800542Notes

Reaction equation

HRID 1800542 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[C:13]([Cl:26])=[CH:14][C:15]([F:25])=[C:16]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])[CH:17]=1)[N:5]=2.[C:27](Cl)(=[O:29])[CH3:28]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:27]([NH:1][C:2]1[S:3][C:4]2[C:9]([N:10]=1)=[CH:8][CH:7]=[C:6]([O:11][C:12]1[C:13]([Cl:26])=[CH:14][C:15]([F:25])=[C:16]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:21])[F:22])[CH:17]=1)[N:5]=2)(=[O:29])[CH3:28]

Participants

5

Reactant 2

HCID 6367Acetyl chlorideHCID 86646019N-{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-chloro-2-fluorophenyl}-2,2,2-trifluoroacetamide

Product 1

HCID 86646020N-(5-{[2-(acetylamino) [1,3]thiazolo[5,4-b]pyridin-5-yl]oxy}-4-chloro-2-fluorophenyl)-2,2,2-trifluoroacetamideYield 96.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of N-{5-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-chloro-2-fluorophenyl}-2,2,2-trifluoroacetamide (2.03 g, 5 mmol) and N,N-dimethylpyridine-4-amine (0.61 g, 5 mmol) in pyridine (10 mL) was added dropwise acetyl chloride (0.78 g, 10 mmol) under ice-cooling, and the mixture was stirred at room temperature for 3 hr. The reaction solution was concentrated under reduced pressure, and the residue was diluted with ethyl acetate (50 mL), washed with water (50 mL×2), and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was washed with diethyl ether, collected by filtration, and dried under reduced pressure to give the title compound (2.16 g, 96%) as white powder crystals.

Workup

  1. temperaturecooling
  2. concentrationThe reaction solution was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate (50 mL)
  4. washwashed with water (50 mL×2)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationThe insoluble material was filtered off
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. washThe obtained residue was washed with diethyl ether
  9. filtrationcollected by filtration
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-3de9940c4b704b2b80b2bc2029ecf1f4
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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