tert-Butoxy bis(dimethylamino)methane → HCID 136066511, compound

HRID 269480Notes

Reaction equation

[C:1]1([CH2:7][C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O[CH:24](N(C)C)[N:25](C)C)(C)(C)C.Cl.NO.C([O-])(=O)C.[Na+].C([O-])(O)=O.[Na+]>C1COCC1>[C:1]1([C:7]2[CH:24]=[N:25][O:9][C:8]=2[C:10]2[C:18]3[C:13](=[N:14][CH:15]=[CH:16][CH:17]=3)[NH:12][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 2-phenyl-1-(1H-pyrrolo[2,3-b]pyridin-3-yl)-ethanone (200 mg, 0.85 mmol) in dry THF (5 mL) was added tert-butoxy-N,N,N′,N′-tetramethyl-methanediamine (Bredereck's reagent) (440 mg, 2.52 mmol). The solution was heated at 60° C. for 3 h and evaporated to dry. The resulting residue was dissolved in ethanol (5 mL). To this ethanol solution was then added hydroxylamine hydrochloride (300 mg, 4.32 mmol) and sodium acetate (420 mg, 5.12 mmol). The mixture was heated under reflux for 10 h, cooled, and poured into aqueous NaHCO3 solution. The crude product was collected by filtration and washed with water. After purification by Gilson HPLC, the pure product was obtained as powder (130 mg, 0.50 mmol, 59%).

Workup

customevaporated
customto dry
dissolutionThe resulting residue was dissolved in ethanol (5 mL)
temperatureThe mixture was heated
temperatureunder reflux for 10 h
temperaturecooled
filtrationThe crude product was collected by filtration
washwashed with water
customAfter purification by Gilson HPLC

Sources & evidence

ORD record: ord-d0e131fb1db248dd9777af615778d0b0
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07446199B2

Reaction notes

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