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

HRID 1398144Notes

Reaction equation

HRID 1398144 reaction equation
CC1C=CC(S(O[CH2:12][C:13]2([C:36]3[CH:41]=[CH:40][C:39]([Cl:42])=[C:38]([Cl:43])[CH:37]=3)[CH2:18][CH2:17][CH2:16][N:15]3[C:19]([C:22]4[CH:27]=[CH:26][C:25]([C:28]5[O:32][C:31]([CH3:33])=[N:30][CH:29]=5)=[C:24]([O:34][CH3:35])[CH:23]=4)=[N:20][N:21]=[C:14]23)(=O)=O)=CC=1.[N-:44]=[N+]=[N-].[Na+].O>CS(C)=O>[Cl:43][C:38]1[CH:37]=[C:36]([C:13]2([CH2:12][NH2:44])[CH2:18][CH2:17][CH2:16][N:15]3[C:19]([C:22]4[CH:27]=[CH:26][C:25]([C:28]5[O:32][C:31]([CH3:33])=[N:30][CH:29]=5)=[C:24]([O:34][CH3:35])[CH:23]=4)=[N:20][N:21]=[C:14]23)[CH:41]=[CH:40][C:39]=1[Cl:42]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86662974HCID 86662974, compound

Product 1

HCID 666040871-{8-(3,4-Dichlorophenyl)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}methanamineYield 48.9%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of {8-(3,4-dichlorophenyl)-3-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridin-8-yl}methyl 4-methylbenzenesulfonate (150 mg) and sodium azide (45.8 mg) in DMSO (2 mL) was stirred at 100° C. for 2 days. Water was added to the reaction mixture, and the precipitated solid was collected by filtration. The solid was dissolved in THF (2 mL)/water (2 mL), diphenylphosphino-polystyrene (1.99 mmol/g, 236 mg) was added, and the mixture was stirred at 60° C. overnight. The reaction mixture was filtered, and the solvent in the filtrate was evaporated under reduced pressure. The residue was recrystallized from hexane/ethyl acetate to give the title compound (55.5 mg).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. dissolutionThe solid was dissolved in THF (2 mL)/water (2 mL), diphenylphosphino-polystyrene (1.99 mmol/g, 236 mg)
  3. additionwas added
  4. stirringthe mixture was stirred at 60° C. overnight
  5. filtrationThe reaction mixture was filtered
  6. customthe solvent in the filtrate was evaporated under reduced pressure
  7. customThe residue was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-0b1c8dd97b74402ab34aac0a81cd9c21
Source dataset
uspto-grants-2014_12
Patent number
US08901309B2

Reaction notes

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