Hydrazine → HCID 86608777, compound

HRID 1508395Notes

Reaction equation

HRID 1508395 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[NH:11][N:10]=[C:9]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[S:8]1)=[N+:2]=[N-:3].[C:26]([N:33]1C=CN=C1)(N1C=CN=C1)=[S:27].[NH2:38]N>C1COCC1>[N:1]([CH2:4][CH2:5][CH2:6][C:7]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[N:11]([C:26](=[S:27])[NH:33][NH2:38])[N:10]=[C:9]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[F:19])[S:8]1)=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 866048312-(3-Azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole

Product 1

HCID 86608777HCID 86608777, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
23 °C

Procedure

2-(3-azidopropyl)-5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazole (577 mg, 1.61 mmol) was dissolved in 8 mL THF, followed by addition of thio-carbonyldiimidazole (458 mg, 2.57 mmol), and heated to reflux for 1 hour. The reaction mixture was cooled to 23° C., and hydrazine (257 mg, 8.03 mmol) was added. The reaction mixture was stirred for 12 hours. The crude reaction mixture was then concentrated and purified by flash column chromatography, eluting with 4:1 (hexanes/ethyl acetate), to afford the desired product (135 mg, 20%).

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 hour
  3. customThe crude reaction mixture
  4. concentrationwas then concentrated
  5. custompurified by flash column chromatography
  6. washeluting with 4:1 (hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-fe01f58ae9534f329435839c8833dc1a
Source dataset
uspto-grants-2015_12
Patent number
US09221841B2

Reaction notes

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