Sodium Bicarbonate → HCID 118378889, compound

HRID 931036Notes

Reaction equation

HRID 931036 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:16]3[O:20][CH:19]=[N:18][CH:17]=3)[C:7]3[N:8]([C:10]([C:13](O)=[O:14])=[CH:11][N:12]=3)[CH:9]=2)[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.[CH:46]12[NH:53][CH:50]([CH2:51][CH2:52]1)[CH2:49][O:48][CH2:47]2.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(N(CC)CC)C>[CH:1]1([C:4]2[CH:5]=[C:6]([C:16]3[O:20][CH:19]=[N:18][CH:17]=3)[C:7]3[N:8]([C:10]([C:13]([N:53]4[CH:46]5[CH2:52][CH2:51][CH:50]4[CH2:49][O:48][CH2:47]5)=[O:14])=[CH:11][N:12]=3)[CH:9]=2)[CH2:3][CH2:2]1

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 534011293-Oxa-8-azabicyclo(3.2.1)octane hydrochlorideHCID 118378870HCID 118378870, compound

Product 1

HCID 118378889HCID 118378889, compoundYield 23.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

6-Cyclopropyl-8-(1,3-oxazol-5-yl)imidazo[1,2-a]pyridine-3-carboxylic acid (135 mg) was dissolved in DMF (4 mL), and HATU (229 mg), 3-oxa-8-azabicyclo[3.2.1]octane hydrochloride (113 mg) and triethylamine (91 μL) were added thereto. The reaction mixture was stirred at room temperature for 1 hr, saturated aqueous sodium bicarbonate solution was added thereto, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane), and the obtained solid was recrystallized from ethyl acetate/hexane to give the title compound (43 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)
  6. customthe obtained solid was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-88b9803bdb42491cacab3caba84e3f80
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Reaction notes

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