Water → HCID 25196226, compound

HRID 2190479Notes

Reaction equation

HRID 2190479 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([NH:19][C:20](=[O:33])[C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])[C:22]=4[Cl:32])[CH:15]=[CH:16][C:17]=3[F:18])[CH:8]=[CH:7][C:5]=2[N:6]=1.[C:34](Cl)(=[O:36])[CH3:35].N1C=CC=CC=1.O>O1CCCC1.C(OCC)(=O)C>[C:34]([NH:1][C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][C:12]3[CH:13]=[C:14]([NH:19][C:20](=[O:33])[C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([C:30]#[N:31])([CH3:29])[CH3:28])[C:22]=4[Cl:32])[CH:15]=[CH:16][C:17]=3[F:18])[CH:8]=[CH:7][C:5]=2[N:6]=1)(=[O:36])[CH3:35]

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 6367Acetyl chlorideHCID 86655406N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-4-fluorophenyl}-2-chloro-3-(1-cyano-1-methylethyl)benzamide

Product 1

HCID 25196226HCID 25196226, compoundYield 28%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-{3-[(2-amino-1,3-benzothiazol-6-yl)oxy]-4-fluorophenyl}-2-chloro-3-(1-cyano-1-methylethyl)benzamide (350 mg, 0.73 mmol) in tetrahydrofuran (20 mL) were added acetyl chloride (63 mg, 0.80 mmol) and pyridine (86 mg, 1.09 mmol), and the mixture was stirred at room temperature for 10 min. To the reaction mixture were added water (100 mL) and ethyl acetate (100 mL). After stirring for 30 min, the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=20/80→0/100), and triturated with ethyl acetate/hexane to give the title compound (105 mg, 28%) as a colorless solid.

Workup

  1. stirringAfter stirring for 30 min
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationthe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=20/80→0/100)
  7. customtriturated with ethyl acetate/hexane

Sources & evidence

ORD record
ord-438c0591143f43bea2a95696a0e70164
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

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