Sodium Bicarbonate → 3-Oxa-8-azabicyclo[3.2.1]oct-8-yl(8-(1,3-oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)methanone

HRID 931049Notes

Reaction equation

HRID 931049 reaction equation
[O:1]1[C:5]([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:4][N:3]=[CH:2]1.F[P-](F)(F)(F)(F)F.C(C(=NO[C+](N(C)C)N1CCOCC1)C(OCC)=O)#N.Cl.[CH:50]12[NH:57][CH:54]([CH2:55][CH2:56]1)[CH2:53][O:52][CH2:51]2.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(N(CC)CC)C>[CH:54]12[N:57]([C:19]([C:16]3[N:8]4[CH:9]=[C:10]([C:12]([F:13])([F:14])[F:15])[CH:11]=[C:6]([C:5]5[O:1][CH:2]=[N:3][CH:4]=5)[C:7]4=[N:18][CH:17]=3)=[O:21])[CH:50]([CH2:56][CH2:55]1)[CH2:51][O:52][CH2:53]2

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 534011293-Oxa-8-azabicyclo(3.2.1)octane hydrochlorideHCID 1183789628-(1,3-Oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acidHCID 178472143HCID 178472143, compound

Product 1

HCID 1183790013-Oxa-8-azabicyclo[3.2.1]oct-8-yl(8-(1,3-oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)methanoneYield 98.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

To a mixture of 8-(1,3-oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid (80 g), triethylamine (113 mL) and DMF (2000 mL) were added (1-cyano-2-ethoxy-2-oxoethylideneaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate (127 g) and 3-oxa-8-azabicyclo[3.2.1]octane hydrochloride (42.3 g) at 0° C., and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added saturated aqueous sodium bicarbonate solution at 0° C. The obtained solid was collected by filtration, and washed with saturated aqueous sodium bicarbonate solution, water, ethanol and methyl tert-butyl ether to give the title compound (104 g).

Workup

  1. filtrationThe obtained solid was collected by filtration
  2. washwashed with saturated aqueous sodium bicarbonate solution, water, ethanol and methyl tert-butyl ether

Sources & evidence

ORD record
ord-13d0acf4265a4864b296c714245693bb
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Reaction notes

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