tert-Butyl methyl ether → HCID 66959019, compound
Reaction equation
Br[C:2]1[C:3]([C:17]#[N:18])=[N:4][N:5]([CH3:16])[C:6]=1[CH2:7][NH:8]C(=O)OC(C)(C)C.[ClH:19].[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1B(O)O.COC(C)(C)C>C(OCC)C>[ClH:19].[NH2:8][CH2:7][C:6]1[N:5]([CH3:16])[N:4]=[C:3]2[C:2]=1[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[N:20]=[C:17]2[NH2:18]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
A modification of the method described in Example 1283 was used to couple tert-butyl (4-bromo-3-cyano-1-methyl-1H-pyrazol-5-yl)methylcarbamate (1.43 g, 4.53 mmol) with 2-aminophenylboronic acid hydrochloride (1.57 g, 9.06 mmol). The reaction was completed in 70 minutes. tert-Butyl methyl ether was used instead of chloroform in the work-up procedure. The coupling product was purified by IFC (silica cartridge, eluting with 40% to 60% ethyl acetate in hexane). The reaction with hydrogen chloride was heated at reflux for 24 hours. Diethyl ether (50 mL) was added after the reaction cooled to room temperature. A precipitate was present and was isolated by filtration and dried on the vacuum filter funnel for three hours to provide 1.13 g of 1-(aminomethyl)-2-methyl-2H-pyrazolo[3,4-c]quinolin-4-amine hydrochloride as a white solid, mp>250° C.
Workup
- customThe coupling product was purified by IFC (silica cartridge, eluting with 40% to 60% ethyl acetate in hexane)
- customThe reaction with hydrogen chloride
- temperaturewas heated
- temperatureat reflux for 24 hours
- customwas isolated by filtration
- customdried on the vacuum
- filtrationfilter funnel for three hours
Sources & evidence
- ORD record
- ord-57e49e77aed9473ba37a1cfdd681cc14
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07544697B2
Reaction notes
Loading…