Water → HCID 91594324, compound

HRID 1800576Notes

Reaction equation

HRID 1800576 reaction equation
[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]2[N:21]=[C:20]3[S:22][C:23]([NH2:25])=[N:24][C:19]3=[CH:18][CH:17]=2)[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[C:27](Cl)(=[O:29])[CH3:28].O>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:1]([O:5][C:6](=[O:26])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([F:14])=[C:10]([O:15][C:16]2[N:21]=[C:20]3[S:22][C:23]([NH:25][C:27](=[O:29])[CH3:28])=[N:24][C:19]3=[CH:18][CH:17]=2)[CH:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 6367Acetyl chlorideHCID 91385505HCID 91385505, compound

Product 1

HCID 91594324HCID 91594324, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a solution of tert-butyl{3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-fluorophenyl}carbamate (0.94 g, 2.5 mmol) and N,N-dimethylpyridine-4-amine (0.31 g, 2.5 mmol) in pyridine (5 mL) was added dropwise acetyl chloride (0.40 g, 5 mmol) under ice-cooling, and the mixture was stirred at room temperature overnight. To the reaction mixture was added water (100 mL), and the mixture was extracted with ethyl acetate (100 mL×2). The ethyl acetate layers were combined, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was triturated with diethyl ether to give the title compound (1.05 g, quantitatively) as a white amorphous.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate (100 mL×2)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe obtained residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-2ab019c81fcf4242832d9d6be9120693
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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