Diisopropylethylamine → HCID 89690351, compound
Reaction equation
[O:1]=[C:2]1[CH2:5][CH:4]([C:6]([OH:8])=O)[CH2:3]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(CC)C(C)C)(C)C.[Br:42][C:43]1[CH:44]=[C:45]([NH:50]C)[C:46]([NH2:49])=[CH:47][CH:48]=1>CN(C=O)C>[NH2:50][C:45]1[CH:44]=[C:43]([Br:42])[CH:48]=[CH:47][C:46]=1[NH:49][C:6]([CH:4]1[CH2:3][C:2](=[O:1])[CH2:5]1)=[O:8]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 3-oxocyclobutanecarboxylic acid (1.1 g) in DMF (50 ml) were added HATU (5.7 g) and N,N-diisopropylethylamine (4.2 ml) at 0° C., and the mixture was allowed to warm to room temperature for 30 min. A solution of 4-bromo-N2-methylbenzene-1,2-diamine (2.0 g) in DMF (2 ml) was added, and the resulting mixture was stirred at room temperature for 18 h. The mixture was concentrated in vacuo and diluted with DCM. The mixture was washed with saturated NH4Cl solution, saturated NaHCO3 solution and brine successively, dried over Na2SO4, concentrated in vacuo and purified by column chromatography (hexane/EtOAc) to afford the title compound (2.7 g) as an off-white solid.
Workup
- concentrationThe mixture was concentrated in vacuo
- additiondiluted with DCM
- washThe mixture was washed with saturated NH4Cl solution, saturated NaHCO3 solution and brine successively
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
- custompurified by column chromatography (hexane/EtOAc)
Sources & evidence
- ORD record
- ord-6ee308dfcf1842678c012ee650986195
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09365540B2
Reaction notes
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