Sodium Bicarbonate → 3-oxa-6-azabicyclo[3.1.1]hept-6-yl(8-(1H-1,2,4-triazol-1-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)methanone

HRID 931048Notes

Reaction equation

HRID 931048 reaction equation
[N:1]1([C:6]2[C:7]3[N:8]([C:16]([C:19]([OH:21])=O)=[CH:17][N:18]=3)[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=2)[CH:5]=[N:4][CH:3]=[N:2]1.FC(F)(F)C(O)=O.[CH:29]12[CH2:35][CH:33]([NH:34]1)[CH2:32][O:31][CH2:30]2.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(N(CC)CC)C>[CH:33]12[CH2:35][CH:29]([N:34]1[C:19]([C:16]1[N:8]3[CH:9]=[C:10]([C:12]([F:14])([F:13])[F:15])[CH:11]=[C:6]([N:1]4[CH:5]=[N:4][CH:3]=[N:2]4)[C:7]3=[N:18][CH:17]=1)=[O:21])[CH2:30][O:31][CH2:32]2

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 118378892HCID 118378892, compoundHCID 118378980HCID 118378980, compound

Product 1

HCID 1183789023-oxa-6-azabicyclo[3.1.1]hept-6-yl(8-(1H-1,2,4-triazol-1-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)methanoneYield 57.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 8-(1H-1,2,4-triazol-1-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid (80 mg), 3-oxa-6-azabicyclo[3.1.1]heptane 2,2,2-trifluoroacetate (75 mg), HATU (133 mg), triethylamine (150 μL) and anhydrous DMF (3 mL) was stirred at room temperature for 12 hr, saturated aqueous sodium bicarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and the obtained solid was recrystallized from ethyl acetate/hexane to give the title compound (59 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extract was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  5. customthe obtained solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-26c40103094144b6bb5719446119ebfc
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Reaction notes

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