Diethyl Ether → HCID 178424516, compound

HRID 1190206Notes

Reaction equation

HRID 1190206 reaction equation
[CH3:1][C:2]1([CH3:36])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][OH:25])[CH2:19][CH2:18]3)([CH3:16])[CH3:15])[CH:11]=[CH:10][C:9]=2[NH:26][C:27]([C:29]2[NH:30][CH:31]=[C:32]([C:34]#[N:35])[N:33]=2)=[O:28])=[CH:4][CH2:3]1.[ClH:37].CCOCC.C(OCC)C>CCO>[ClH:37].[CH3:1][C:2]1([CH3:36])[CH2:7][CH2:6][C:5]([C:8]2[CH:13]=[C:12]([C:14]([N:17]3[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][OH:25])[CH2:19][CH2:18]3)([CH3:15])[CH3:16])[CH:11]=[CH:10][C:9]=2[NH:26][C:27]([C:29]2[NH:30][CH:31]=[C:32]([C:34]#[N:35])[N:33]=2)=[O:28])=[CH:4][CH2:3]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 10953452Ether hydrochlorideHCID 178424515HCID 178424515, compound

Product 1

HCID 178424516HCID 178424516, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-cyano-1H-imidazole-2-carboxylic acid (2-(4,4-dimethyl-cyclohex-1-enyl)-4-{1-[4-(2-hydroxy-ethyl)-piperazin-1-yl]-1-methyl-ethyl}-phenyl)-amide (as prepared in Example 62, 162.0 mg, 0.330 mmol) in 2 mL of EtOH was added a 2 N HCl ether solution (165 μL, 0.330 mmol). The mixture was stirred at RT for 0.5 h, 1 mL of diethyl ether (Et2O) was added and the resulting mixture was heated at 60° C. for 1 min until the solution turned clear. The mixture was cooled down to RT and the solid was collected by filtration and washed with Et2O. Upon drying in vacuo, the title compound (92 mg, 53%) was obtained as an off-white solid. 1H-NMR (CD3OD; 400 MHz): δ 8.42 (d, 1H, J=8.6 Hz), 8.04 (s, 1H), 7.70 (dd, 1H, J=8.6, 2.0 Hz), 7.64 (br s, 1H), 5.83 (m, 1H), 3.91 (m, 2H), 3.40-3.93 (m, 4H), 3.37 (m, 2H), 2.33-2.40 (m, 2H), 2.05-2.12 (m, 2H), 1.72-2.00 (br s, 6H), 1.62 (t, 2H, J=6.5 Hz), 1.07 (s, 6H). Mass spectrum (ESI, m/z): Calcd. for C28H38N6O2, 491.3 (M+H). found 491.1.

Workup

  1. temperaturethe resulting mixture was heated at 60° C. for 1 min until the solution
  2. temperatureThe mixture was cooled down to RT
  3. filtrationthe solid was collected by filtration
  4. washwashed with Et2O
  5. customUpon drying in vacuo

Sources & evidence

ORD record
ord-a7fe3313303f42bbaff9985354c7e458
Source dataset
uspto-grants-2014_03
Patent number
US08674100B2

Reaction notes

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