Thionyl Chloride → HCID 57749087, compound

HRID 1874462Notes

Reaction equation

HRID 1874462 reaction equation
[CH3:1][C:2]1[S:3][C:4]([CH3:10])=[C:5]([C:7]([OH:9])=O)[N:6]=1.S(Cl)(Cl)=O.[NH2:15][C:16]1[CH:17]=[C:18]([CH:35]=[CH:36][C:37]=1[CH3:38])[O:19][C:20]1[CH:21]=[CH:22][C:23]2[N:24]([N:26]=[C:27]([NH:29][C:30]([CH:32]3[CH2:34][CH2:33]3)=[O:31])[N:28]=2)[CH:25]=1>O1CCCC1.CN(C)C=O.C(=O)([O-])O.[Na+]>[CH:32]1([C:30]([NH:29][C:27]2[N:28]=[C:23]3[CH:22]=[CH:21][C:20]([O:19][C:18]4[CH:35]=[CH:36][C:37]([CH3:38])=[C:16]([NH:15][C:7]([C:5]5[N:6]=[C:2]([CH3:1])[S:3][C:4]=5[CH3:10])=[O:9])[CH:17]=4)=[CH:25][N:24]3[N:26]=2)=[O:31])[CH2:33][CH2:34]1

Participants

7

Reactant 3

HCID 24386Thionyl ChlorideHCID 138353132,5-Dimethyl-1,3-thiazole-4-carboxylic acidHCID 57749401N-[6-(3-amino-4-methylphenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide

Product 1

HCID 57749087HCID 57749087, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 8028TetrahydrofuranSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 2,5-dimethyl-1,3-thiazole-4-carboxylic acid (107 mg, 0.681 mmol) in tetrahydrofuran (5 mL) were added N,N-dimethylformamide (2 drops) and thionyl chloride (118 μL, 1.36 mmol), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in N,N-dimethylacetamide (6 mL). N-[6-(3-Amino-4-methylphenoxy)[1,2,4]triazolo[1,5-a]pyridin-2-yl]cyclopropanecarboxamide (200 mg, 0.619 mmol) was added thereto, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, the residue was and recrystallized from ethanol to give the title compound (248 mg, 87%) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in N,N-dimethylacetamide (6 mL)
  3. stirringthe mixture was stirred at room temperature for 2 hr
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltrated
  8. concentrationThe filtrate was concentrated under reduced pressure
  9. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-179121824d484c51937247734b852708
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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