tert-Butoxy bis(dimethylamino)methane → HCID 135454941, compound
Reaction equation
[CH2:1]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]2[CH:16]=[C:17]3[C:23]([C:24](=[O:34])[CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=4[F:33])=[CH:22][NH:21][C:18]3=[N:19][CH:20]=2)[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O[CH:40](N(C)C)[N:41](C)C)(C)(C)C.Cl.NO.C([O-])(=O)C.[Na+]>C1COCC1>[CH2:1]([NH:8][CH:9]1[CH2:14][CH2:13][C:12]([C:15]2[CH:16]=[C:17]3[C:23]([C:24]4[O:34][N:41]=[CH:40][C:25]=4[C:26]4[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[C:27]=4[F:33])=[CH:22][NH:21][C:18]3=[N:19][CH:20]=2)=[CH:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
6
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 1-[5-(4-benzylamino-cyclohexyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-2-(2,3-difluoro-phenyl)-ethanone (150 mg, 0.27 mmol. Preparation: see below) and t-butoxybis(dimethylamino)methane (0.27 ml, 1.0 mmol, Brederck's reagent) in THF (5 ml) was heated at 60° C. for 2 h. The reaction mixture was concentrated and dried under high vacuum for 0.5 h. The residue was dissolved in Ethanol (10 ml), refluxed with hydroxylamine hydrogen chloride (94 mg, 1.35 mmol) and sodium acetate (1.62 mmol) for 2.5 h. The mixture was concentrated and suspended in satd. NaHCO3 and filtered. The solid was further purified by chromatography to give 50 mg of the desired product in 38.4% yield.
Workup
- concentrationThe reaction mixture was concentrated
- customdried under high vacuum for 0.5 h
- dissolutionThe residue was dissolved in Ethanol (10 ml)
- concentrationThe mixture was concentrated
- filtrationNaHCO3 and filtered
- customThe solid was further purified by chromatography
Sources & evidence
- ORD record
- ord-619167bb0a0345d58f1c1d0c5f2245b4
- Source dataset
- uspto-grants-2008_11
- Patent number
- US07446199B2
Reaction notes
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