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 1424073Notes

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

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

temperatureThe reaction mixture was cooled to room temperature
distillationthe solvent was distilled off
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

Loading…