Hydrazine → HCID 86608766, compound

HRID 1508377Notes

Reaction equation

HRID 1508377 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[S:13][C:12]([CH2:20][CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:11][N:10]=1.[N:31]1([C:36](N2C=CN=C2)=[S:37])C=CN=C1.[NH2:43]N>C1COCC1>[C:26]([O:25][C:24]([NH:23][CH2:22][CH2:21][CH2:20][C:12]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:11]([C:36](=[S:37])[NH:31][NH2:43])[N:10]=[C:9]([C:3]2[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=2[F:1])[S:13]1)=[O:30])([CH3:27])([CH3:29])[CH3:28]

Participants

5

Reactant 3

HCID 9321HydrazineHCID 802641,1'-ThiocarbonyldiimidazoleHCID 67214570HCID 67214570, compound

Product 1

HCID 86608766HCID 86608766, compoundYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of tert-butyl 3-(5-(2,5-difluorophenyl)-2-phenyl-2,3-dihydro-1,3,4-thiadiazol-2-yl)propylcarbamate (0.123 g, 0.284 mmol) in THF (2 mL) was added di(1H-imidazol-1-yl)methanethione (0.061 g, 0.340 mmol). After heating to 70° C. for 2 hours, the reaction mixture was cooled to room temperature and treated with hydrazine (0.027 g, 0.851 mmol). After stirring for 1 hour, the mixture was concentrated under reduced pressure and chromatographed (10:1 hexanes/ethyl acetate) to provide the product (0.036 g, 25%).

Workup

  1. temperaturethe reaction mixture was cooled to room temperature
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customchromatographed (10:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-9736d3d848af4c60b3b99542a5b49ab2
Source dataset
uspto-grants-2015_12
Patent number
US09221841B2

Reaction notes

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