Water → 8-[5-(3,4-Dichlorophenyl)-1,3,4-oxadiazol-2-yl]-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-methyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine

HRID 71150Notes

Reaction equation

HRID 71150 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:15]2[N:19]3[CH2:20][CH2:21][CH2:22][C:23]([CH3:27])([C:24](O)=[O:25])[C:18]3=[N:17][N:16]=2)[CH:6]=[CH:7][C:8]=1[C:9]1[O:13][C:12]([CH3:14])=[N:11][CH:10]=1.Cl.[Cl:29][C:30]1[CH:31]=[C:32]([CH:37]=[CH:38][C:39]=1[Cl:40])[C:33]([NH:35][NH2:36])=O.C(N(CC)CC)C.O>CN(C=O)C>[Cl:29][C:30]1[CH:31]=[C:32]([C:33]2[O:25][C:24]([C:23]3([CH3:27])[CH2:22][CH2:21][CH2:20][N:19]4[C:15]([C:5]5[CH:6]=[CH:7][C:8]([C:9]6[O:13][C:12]([CH3:14])=[N:11][CH:10]=6)=[C:3]([O:2][CH3:1])[CH:4]=5)=[N:16][N:17]=[C:18]34)=[N:36][N:35]=2)[CH:37]=[CH:38][C:39]=1[Cl:40]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 666082883-[3-Methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-methyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylic acidHCID 666083733,4-Dichlorobenzohydrazide hydrochloride

Product 1

HCID 666039538-[5-(3,4-Dichlorophenyl)-1,3,4-oxadiazol-2-yl]-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-methyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridineYield 26.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-8-methyl-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-carboxylic acid (100 mg), 3,4-dichlorobenzohydrazide hydrochloride (79 mg) and triethylamine (114 μL) in DMF (1.5 mL) was stirred at room temperature for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was dissolved in acetonitrile (1.5 mL), trichloroacetonitrile (114 μL) and triphenylphosphine (286 mg) were added, and the mixture was stirred at 70° C. for 2 hr. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane) to give the title compound (38.8 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in acetonitrile (1.5 mL)
  6. additiontrichloroacetonitrile (114 μL) and triphenylphosphine (286 mg) were added
  7. stirringthe mixture was stirred at 70° C. for 2 hr
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (NH, ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d8ddea4fb62b4503942269fdca2c858d
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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