N,N'-Dimethylethylenediamine → HCID 16048984, compound

HRID 1364162Notes

Reaction equation

HRID 1364162 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.[CH3:22][N:23]1[CH2:29][C:27](=[O:28])[NH:26][C:24]1=[O:25].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:26]5[C:27](=[O:28])[CH2:29][N:23]([CH3:22])[C:24]5=[O:25])=[CH:3][CH:4]=4)[N:9]=[C:10]3[CH2:11][CH2:12]2)[CH2:21][CH2:20][CH2:19]1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 692171-MethylhydantoinHCID 16048914HCID 16048914, compound

Product 1

HCID 16048984HCID 16048984, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °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) (80 mg, 0.23 mmol), 1-methylhydantoin (52 mg, 0.46 mmol), potassium carbonate (95 mg, 0.7 mmol), copper (I) iodide (13 mg, 0.07 mmol) and N,N′-dimethyl-1,2-ethanediamine (8 μl, 0.07 mmol) in dioxane (2 ml) was heated in the microwave (normal absorption) at 150° C. for 2 hours. The reaction mixture was purified by SCX cartridge, followed by Mass Directed Autopreparation and column chromatography on silica gel, eluting with a mixture of 2M ammonia in methanol/dichloromethane (0-5%) to afford the title compound (E38). MS (ES+) m/e 380 [M+H]+.

Workup

  1. customThe reaction mixture was purified by SCX cartridge
  2. washeluting with a mixture of 2M ammonia in methanol/dichloromethane (0-5%)

Sources & evidence

ORD record
ord-6e07fef232094d719d7dd76e6db7b67d
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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