Hydrazine → HCID 86608775, compound

HRID 2387618Notes

Reaction equation

HRID 2387618 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2([CH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[NH:19][N:18]=[C:17]([C:20]3[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=3[F:27])[S:16]2)[CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:39]([N:46]1C=CN=C1)(N1C=CN=C1)=[S:40].[NH2:51]N>C1COCC1>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2([CH2:28][CH2:29][CH2:30][NH:31][C:32](=[O:38])[O:33][C:34]([CH3:37])([CH3:36])[CH3:35])[N:19]([C:39]([NH:46][NH2:51])=[S:40])[N:18]=[C:17]([C:20]3[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=3[F:27])[S:16]2)[CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 68507256HCID 68507256, compound

Product 1

HCID 86608775HCID 86608775, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl 3-(2-(3-(tert-butyldimethylsilyloxy)phenyl)-5-(2,5-difluorophenyl)-2,3-dihydro-1,3,4-thiadiazol-2-yl)propylcarbamate (0.845 g, 1.50 mmol) was weighed into a 25 mL flask and suspended in 10 mL of anhydrous THF, followed by addition of thiocarbonyldiimidazole (0.294 g, 1.65 mmol). The reaction mixture was then heated to reflux for 3 hours. The reaction was cooled to room temperature, and then hydrazine (0.235 mL7.50 mmol) was added and the reaction mixture was stirred for 4 hours at room temperature. The reaction mixture was concentrated, and the residue was loaded onto Biotage (flash column chromatography 10-50% ethyl acetate/hexanes) to provide 143 mg (80% purity) of the desired product.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-326a2ac13cdb4174876dd988860804bc
Source dataset
uspto-grants-2012_09
Patent number
US08268871B2

Reaction notes

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