Benzenecarbothioic acid, 2,5-difluoro-, hydrazide → HCID 68507256, compound

HRID 2387617Notes

Reaction equation

HRID 2387617 reaction equation
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([C:15](=O)[CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[F:28][C:29]1[CH:38]=[CH:37][C:36]([F:39])=[CH:35][C:30]=1[C:31](=[S:34])[NH:32][NH2:33]>CCO.C(Cl)Cl>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([C:15]2([CH2:16][CH2:17][CH2:18][NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[NH:33][N:32]=[C:31]([C:30]3[CH:35]=[C:36]([F:39])[CH:37]=[CH:38][C:29]=3[F:28])[S:34]2)[CH:12]=[CH:13][CH:14]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 55279024Benzenecarbothioic acid, 2,5-difluoro-, hydrazideHCID 68503911HCID 68503911, compound

Product 1

HCID 68507256HCID 68507256, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 21584144Dichloromethane ethanolSolvent

Procedure

To a solution of tert-butyl 4-(3-(tert-butyldimethylsilyloxy)phenyl)-4-oxobutylcarbamate (1.400 g, 3.55 mmol) in 20 mL of a 3:1 EtOH/DCM mixture was added 2,5-difluorobenzothiohydrazide (0.704 g, 3.74 mmol). The reaction was stirred overnight at room temperature, then heated to 45° C. for 10 hours. The reaction mixture was then concentrated in vacuo, loaded directly to Biotage (45), followed by flash column chromatography (20-50% ethyl acetate/hexanes), yielding the desired product as a yellow semi-solid (1.742 g, 82%).

Workup

  1. temperatureheated to 45° C. for 10 hours
  2. concentrationThe reaction mixture was then concentrated in vacuo

Sources & evidence

ORD record
ord-1d445eab305c4edeb0fcd587cbae8114
Source dataset
uspto-grants-2012_09
Patent number
US08268871B2

Reaction notes

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