3-(Trifluoromethyl)benzoyl chloride → HCID 59507021, compound

HRID 1800435Notes

Reaction equation

HRID 1800435 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:24][CH3:25])=[C:6]([CH:23]=1)[O:7][C:8]1[N:13]=[C:12]2[S:14][C:15]([NH:17][C:18]([CH:20]3[CH2:22][CH2:21]3)=[O:19])=[N:16][C:11]2=[CH:10][CH:9]=1.[F:26][C:27]([F:38])([F:37])[C:28]1[CH:29]=[C:30]([CH:34]=[CH:35][CH:36]=1)[C:31](Cl)=[O:32]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[CH:20]1([C:18]([NH:17][C:15]2[S:14][C:12]3[C:11]([N:16]=2)=[CH:10][CH:9]=[C:8]([O:7][C:6]2[CH:23]=[C:2]([NH:1][C:31](=[O:32])[C:30]4[CH:34]=[CH:35][CH:36]=[C:28]([C:27]([F:26])([F:37])[F:38])[CH:29]=4)[CH:3]=[CH:4][C:5]=2[O:24][CH3:25])[N:13]=3)=[O:19])[CH2:21][CH2:22]1

Participants

5

Reactant 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 86645994HCID 86645994, compound

Product 1

HCID 59507021HCID 59507021, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent2×

Procedure

To a solution of N-[5-(5-amino-2-methoxyphenoxy)[1,3]thiazolo[5,4-b]pyridin-2-yl]cyclopropanecarboxamide (93.0 mg, 261 μmol) in pyridine (2 mL) were added a solution of 3-(trifluoromethyl)benzoyl chloride prepared above in pyridine (3 mL) and N,N-dimethylpyridine-4-amine (28.9 mg, 237 μmol), and the mixture was stirred at room temperature for 14 hr. The reaction solution was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate (50 mL). The solution was washed with 0.1N hydrochloric acid (30 mL) and saturated aqueous sodium hydrogen carbonate solution (30 mL), and dried over anhydrous magnesium sulfate, the insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (ethyl acetate/hexane=2/98→80/20) to give the title compound (79 mg, 58%) as a white powder.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in ethyl acetate (50 mL)
  3. washThe solution was washed with 0.1N hydrochloric acid (30 mL) and saturated aqueous sodium hydrogen carbonate solution (30 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationthe insoluble material was filtered off
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-efb465c926474f5382a5126cad0f73b4
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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