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Diisopropyl Ether → 8-[(2,6-difluorobenzyl)oxy]-N-[2-(5-ethyl-1,3,4-oxadiazol-2-yl)-1-hydroxypropan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide

HRID 923516
Notes
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Reaction equation

HRID 923516 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([OH:18])=O)=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1.FC(F)(F)C(O)=O.[NH2:31][C:32]([C:36]1[O:37][C:38]([CH2:41][CH3:42])=[N:39][N:40]=1)([CH3:35])[CH2:33][OH:34].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC.C(OC(C)C)(C)C>C(OCC)(=O)C.O.CN(C=O)C>[F:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:3]=1[CH2:4][O:5][C:6]1[C:7]2[N:8]([C:12]([C:16]([NH:31][C:32]([C:36]3[O:37][C:38]([CH2:41][CH3:42])=[N:39][N:40]=3)([CH3:35])[CH2:33][OH:34])=[O:18])=[C:13]([CH3:15])[N:14]=2)[CH:9]=[CH:10][CH:11]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

10

Reactant 6

HCID 7914Diisopropyl EtherHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 867178728-((2,6-Difluorobenzyl)oxy)-2-methylimidazo[1,2-a]pyridine-3-carboxylic acidHCID 118308732
2-Amino-2-(5-ethyl-1,3,4-oxadiazol-2-yl)propan-1-ol trifluoroacetate

Product 1

HCID 1183087588-[(2,6-difluorobenzyl)oxy]-N-[2-(5-ethyl-1,3,4-oxadiazol-2-yl)-1-hydroxypropan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamideYield 24.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 165 mg of 8-[(2,6-difluorobenzyl)oxy]-2-methylimidazo[1,2-a]pyridine-3-carboxylic acid, 160 mg of 2-amino-2-(5-ethyl-1,3,4-oxadiazol-2-yl)propan-1-ol trifluoroacetate, 90 mg of 1-hydroxybenzotriazole, 0.35 ml of diisopropylethylamine, and 4 ml of DMF was added 130 mg of N-[3-(dimethylamino)propyl]-N′-ethylcarbodiimide hydrochloride, followed by stirring at room temperature overnight. To the reaction mixture was added water, followed by extraction with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was then evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography. To the obtained crude product were added ethyl acetate and diisopropyl ether, and the insoluble materials were collected by filtration, and dried under reduced pressure to obtain 59 mg of 8-[(2,6-difluorobenzyl)oxy]-N-[2-(5-ethyl-1,3,4-oxadiazol-2-yl)-1-hydroxypropan-2-yl]-2-methylimidazo[1,2-a]pyridine-3-carboxamide.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materiala saturated aqueous sodium chloride solution, and the organic layer was dried over anhydrous magnesium sulfate
  4. customThe solvent was then evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography
  6. customTo the obtained crude product
  7. filtrationthe insoluble materials were collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-58de55175c024a83937d94d72071cada
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09278968B2

Reaction notes

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