Dimethylformamide → HCID 59507051, compound

HRID 1800441Notes

Reaction equation

HRID 1800441 reaction equation
[O:1]1[CH:5]=[C:4]([C:6]([OH:8])=O)[N:3]=[CH:2]1.C(Cl)(=O)C(Cl)=O.CN(C)C=O.[NH2:20][C:21]1[S:22][C:23]2[C:28]([N:29]=1)=[CH:27][CH:26]=[C:25]([O:30][C:31]1[CH:32]=[C:33]([NH:38][C:39](=[O:50])[C:40]3[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:49])([F:48])[F:47])[CH:41]=3)[CH:34]=[CH:35][C:36]=1[CH3:37])[N:24]=2>O1CCCC1.N1C=CC=CC=1.O>[CH3:37][C:36]1[CH:35]=[CH:34][C:33]([NH:38][C:39](=[O:50])[C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([C:46]([F:47])([F:48])[F:49])[CH:41]=2)=[CH:32][C:31]=1[O:30][C:25]1[N:24]=[C:23]2[S:22][C:21]([NH:20][C:6]([C:4]3[N:3]=[CH:2][O:1][CH:5]=3)=[O:8])=[N:29][C:28]2=[CH:27][CH:26]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 142814301,3-Oxazole-4-carboxylic acidHCID 86645995HCID 86645995, compound

Product 1

HCID 59507051HCID 59507051, compoundYield 84.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,3-oxazole-4-carboxylic acid (126 mg, 1.12 mmol) in tetrahydrofuran (5 mL) were added oxalyl chloride (118 μL, 1.35 mmol) and N,N-dimethylformamide (20 μL), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated under reduced pressure, the obtained residue and N-{3-[(2-amino[1,3]thiazolo[5,4-b]pyridin-5-yl)oxy]-4-methylphenyl}-3-(trifluoromethyl)benzamide (200 mg, 0.450 mmol) produced in Example C8(iv) were dissolved in pyridine (5 mL), and the solution was stirred at room temperature for 18 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate, and filtrated. The solvent was evaporated under reduced pressure, and the residue was precipitated with tetrahydrofuran to give the title compound (205 mg, 84%) as a white powder.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. stirringthe solution was stirred at room temperature for 18 hr
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was precipitated with tetrahydrofuran

Sources & evidence

ORD record
ord-bbdc63304b894dc1ab94c365c149f865
Source dataset
uspto-grants-2013_01
Patent number
US08344135B2

Reaction notes

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