N,N'-Dimethylethylenediamine → HCID 16048916, compound

HRID 1364161Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:17]=[C:16]3[C:10]([CH2:11][CH2:12][N:13]([CH:18]4[CH2:21][CH2:20][CH2:19]4)[CH2:14][CH2:15]3)=[N:9]2)=[CH:4][CH:3]=1.[O:22]1[CH2:26][CH2:25][NH:24][C:23]1=[O:27].C(=O)([O-])[O-].[K+].[K+].CNCCNC>O1CCOCC1.[Cu]I>[CH:18]1([N:13]2[CH2:14][CH2:15][C:16]3=[CH:17][N:8]([C:5]4[CH:6]=[CH:7][C:2]([N:24]5[CH2:25][CH2:26][O:22][C:23]5=[O:27])=[CH:3][CH:4]=4)[N:9]=[C:10]3[CH2:11][CH2:12]2)[CH2:21][CH2:20][CH2:19]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-(4-bromophenyl)-6-cyclobutyl-2,4,5,6,7,8-hexahydropyrazolo[3,4-d]azepine (may be prepared as described in Example 35) (42 mg, 0.12 mmol), 2-oxazolidinone (21 mg, 0.24 mmol), potassium carbonate (50 mg, 0.36 mmol), copper (I) iodide (8.0 mg, 0.04 mmol) and N,N′-dimethyl-1,2-ethanediamine (5 μl, 0.04 mmol) in dioxane (1.5 ml) was heated in the microwave (high absorption) at 100° C. for 30 minutes. The same amounts again of 2-oxazolidinone, potassium carbonate, copper (I) iodide and N,N′-dimethyl-1,2-ethanediamine were added and the mixture heated in the microwave at 150° C. for 4 hours. The reaction mixture was evaporated in vacuo, then purified by SCX cartridge, followed by Mass Directed Autopreparation to afford the title compound (E37). MS (ES+) m/e 353 [M+H]+.

Workup

temperaturethe mixture heated in the microwave at 150° C. for 4 hours
customThe reaction mixture was evaporated in vacuo
custompurified by SCX cartridge

Sources & evidence

ORD record: ord-26bfdf43fed34ae7a875fabb7e48888e
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888347B2

Reaction notes

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