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

HRID 1424073
Notes
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Reaction equation

HRID 1424073 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 432446091-(4-Bromophenyl)cyclopropane-1-carbohydrazideHCID 71466071(7R)-7-({[t-Butyl(dimethyl)silyl]oxy}methyl)-7-methyl-5-(methylthio)-2,3,6,7-tetrahydro-1,4-thiazepine

Product 1

HCID 86712920(8R)-3-[1-(4-Bromophenyl)cyclopropyl]-8-({[t-butyl(dimethyl)silyl]oxy}methyl)-8-methyl-5,6,8,9-tetrahydro[1,2,4]triazolo[4,3-d][1,4]thiazepineYield 86.9%

Reagents, catalysts & solvents 1

HCID 263
1-Butanol
Solvent

Conditions

Temperature
140 °C

Procedure

The compound (1.02 g, 3.19 mmol) obtained in Example 4-1) and the compound (0.81 g, 3.19 mmol) obtained in Example 16-3) were dissolved in 1-butanol (5 mL), and the mixture was stirred at 140° C. for 6 h under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, then the solvent was distilled off, and the obtained residue was purified by silica gel column chromatography (elution solvent: methanol/ethyl acetate=0% to 20%) to obtain the title compound (1.41 g, 85%) in a white solid form.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. distillationthe solvent was distilled off
  3. customthe obtained residue was purified by silica gel column chromatography (elution solvent: methanol/ethyl acetate=0% to 20%)

Sources & evidence

ORD record
ord-a3c28dfdf2914af083e81189be5d6444
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08927536B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes