Sodium Hydroxide → 2-(1,1-dimethylethyl)cyclohepta[d]imidazol-4(1H)-one

HRID 1946478

Reaction equation

[OH-].[Na+].CC1C=CC(S(O[C:14]2[C:20](=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=O)=O)=CC=1.[CH3:22][C:23]([C:26]([NH2:28])=[NH:27])([CH3:25])[CH3:24].Cl.[NH4+].[Cl-]>O.C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:22][C:23]([C:26]1[NH:28][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:20](=[O:21])[C:14]=2[N:27]=1)([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 30 °C

Procedure

To a mixture of sodium hydroxide 30% in water (12.06 g) and toluene (20 mL), tropolone tosylate (2.5 g), tert-butylcarbamidine hydrochloride (1.236 g) and tetrabutylammonium bromide (1.167 g) were added successively and the RM was stirred and heated at 30° C. for 1 hour. The reaction mixture was cooled down to room temp, diluted with an excess of sat. aq. NH4Cl solution and then extracted with EtOAc (3×50 ml). The combined organics were dried (hydrophobic frit) and concentrated under vacuum. The residue was purified by reverse phase chromatography using an acetonitrile-0.1% TFA:water-0.1% TFA (5%-95% gross gradient). The desired fractions were combined and concentrated under vacuum to yield the title compound (1.9 g). LC/MS MH+ 203, Rt 0.62 min (2 minute run).

Workup

additionwere added successively
temperatureThe reaction mixture was cooled down to room temp
extractionextracted with EtOAc (3×50 ml)
customThe combined organics were dried (hydrophobic frit)
concentrationconcentrated under vacuum
customThe residue was purified by reverse phase chromatography
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-4e5f0a65ef3f434fbcc152c02cbbe354
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399444B2

Linked notes

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