Sodium Bicarbonate → ((3S)-3-Hydroxypyrrolidin-1-yl) (8-(1,3-oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)methanone

HRID 931016Notes

Reaction equation

HRID 931016 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.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH:46]1[CH2:50][CH2:49][C@H:48]([OH:51])[CH2:47]1.C(=O)(O)[O-].[Na+]>CN(C=O)C.C(N(CC)CC)C>[OH:51][C@H:48]1[CH2:49][CH2:50][N:46]([C:19]([C:16]2[N:8]3[CH:9]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:11]=[C:6]([C:5]4[O:1][CH:2]=[N:3][CH:4]=4)[C:7]3=[N:18][CH:17]=2)=[O:21])[CH2:47]1

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 2733874(3S)-pyrrolidin-3-olHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 1183789628-(1,3-Oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid

Product 1

HCID 118378931((3S)-3-Hydroxypyrrolidin-1-yl) (8-(1,3-oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridin-3-yl)methanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

8-(1,3-Oxazol-5-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-3-carboxylic acid (1.77 g) was dissolved in DMF (22 mL), and HATU (2.72 g), (S)-pyrrolidin-3-ol (529 μL) and triethylamine (1.08 mL) 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 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 (ethyl acetate/hexane) to give a solid (1.38 g). The solid (100 mg) was recrystallized from ethyl acetate/hexane to give the title compound (89 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with 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 (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-58e09728c85c4e6dba0097f525974d63
Source dataset
uspto-grants-2016_03
Patent number
US09296746B2

Reaction notes

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