Water → 2-(3-azidopropyl)-5-(2,5-difluorophenyl)-3-(3-methyl-1H-1,2,4-triazol-5-yl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole

HRID 2040383Notes

Reaction equation

HRID 2040383 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:11]([C:12](SC)=[NH:13])[N:10]=[C:9]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])[S:8]1)=[N+:2]=[N-:3].[C:30]([NH:33]N)(=O)[CH3:31].O.[N:36]1C=CC=CC=1>>[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[N:11]([C:12]2[NH:13][N:33]=[C:30]([CH3:31])[N:36]=2)[N:10]=[C:9]([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])[S:8]1)=[N+:2]=[N-:3]

Participants

5

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 14039Acetohydrazide2×HCID 86608780methyl 2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazole-3(2H)-carbimidothioate

Product 1

HCID 1784346302-(3-azidopropyl)-5-(2,5-difluorophenyl)-3-(3-methyl-1H-1,2,4-triazol-5-yl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-1,3,4-thiadiazole-3(2H)-carbimidothioate (0.034 g, 0.079 mmol) in 1 mL pyridine was added acetohydrazide (0.017 g, 0.240 mmol). The mixture was warmed to 80° C. and stirred for 16 hours, then treated with acetohydrazide (0.050 g) and stirred at reflux for 40 hours. The cooled mixture was treated with water (10 mL) and extracted with EtOAc (3×10 mL). The combined organic phases were washed with water (10 mL) and brine (10 mL), then dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (10-20% ethyl acetate/hexanes) to afford the desired product as a pale yellow solid, 0.010 g, 29%.

Workup

  1. stirringstirred
  2. temperatureat reflux for 40 hours
  3. extractionextracted with EtOAc (3×10 mL)
  4. washThe combined organic phases were washed with water (10 mL) and brine (10 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash column chromatography (10-20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ab664ee0c5e0468db9690050af1627bd
Source dataset
uspto-grants-2013_11
Patent number
US08580828B2

Reaction notes

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