1-(4-Bromophenyl)cyclopropane-1-carbohydrazide → 3-[1-(4-Bromophenyl)cyclopropyl]-8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepine

HRID 1424006Notes

Reaction equation

HRID 1424006 reaction equation
[Si:1]([O:8][CH2:9][C:10]1([CH3:19])[S:16][CH2:15][CH2:14][N:13]=[C:12](SC)[CH2:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Br:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2([C:30]([NH:32][NH2:33])=O)[CH2:29][CH2:28]2)=[CH:23][CH:22]=1>C(O)CCC>[Br:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2([C:30]3[N:13]4[CH2:14][CH2:15][S:16][C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])([CH3:19])[CH2:11][C:12]4=[N:33][N:32]=3)[CH2:29][CH2:28]2)=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 432446091-(4-Bromophenyl)cyclopropane-1-carbohydrazideHCID 685222157-({[t-Butyl(dimethyl)silyl]oxy}methyl)-7-methyl-5-methylthio-2,3,6,7-tetrahydro-1,4-thiazepine

Product 1

HCID 867128583-[1-(4-Bromophenyl)cyclopropyl]-8-({[tert-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepineYield 66.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 7-({[tert-butyl(dimethyl)silyl]oxy}methyl)-7-methyl-5-(methylthio)-2,3,6,7-tetrahydro-1,4-thiazepine (34.4 g, 108 mmol) and the compound (27.5 g, 108 mmol) obtained in Example 16-3) in 1-butanol (800 mL) was stirred at 140° C. for 6 h. The reaction mixture was cooled to room temperature, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1 to 1:0) to obtain the title compound (36.3 g, 66%) as a white solid.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:1 to 1:0)

Sources & evidence

ORD record
ord-59921c64e43d478aac42652d33d528e6
Source dataset
uspto-grants-2015_01
Patent number
US08927536B2

Reaction notes

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