Ethane, 1-chloro-2-ethoxy- → HCID 21697477, compound

HRID 379456Notes

Reaction equation

HRID 379456 reaction equation
[CH3:1][N:2]([CH2:11][CH:12]([C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=1)[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([C:21]([C:23]2[NH:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[N:24]=2)=[O:22])[CH2:17][CH2:16]1)[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:40]([O:42][CH2:43][CH2:44]Cl)[CH3:41].N12CCCN=C1CCCCC2>C(#N)C.C(OCC)(=O)C>[CH3:1][N:2]([CH2:11][CH:12]([C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[C:34]([Cl:39])[CH:33]=1)[CH2:13][CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([C:21]([C:23]2[N:24]([CH2:41][CH2:40][O:42][CH2:43][CH3:44])[C:25]3[CH:31]=[CH:30][CH:29]=[CH:28][C:26]=3[N:27]=2)=[O:22])[CH2:17][CH2:16]1)[C:3](=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 12341Ethane, 1-chloro-2-ethoxy-HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10187951HCID 10187951, compound

Product 1

HCID 21697477HCID 21697477, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Combine N-methyl-N-(4-(4-(1H-benzimidazole-2-carbonyl)piperidin-1-yl)-2-(3,4-dichlorophenyl)butyl)-benzamide (1.36 mmol), 2-chloroethyl ethyl ether (0.59 g, 5.44 mmol), and 1,8-diazabicyclo[5.4.0]undec-7-ene (1.66 g, 10.9 mmol) in acetonitrile (16 mL). Heat to reflux. After 18 hours, cool to ambient temperature and dilute the reaction mixture with ethyl acetate. Extract twice with saturated aqueous solution of ammonium chloride, 5% aqueous solution of sodium bicarbonate, water, and saturated aqueous solution of sodium chloride. Dry the organic layer over Na2SO4, filter, and concentrate invacuo to give the title compound.

Workup

  1. temperatureHeat to reflux
  2. extractionExtract twice with saturated aqueous solution of ammonium chloride, 5% aqueous solution of sodium bicarbonate, water, and saturated aqueous solution of sodium chloride
  3. dry with materialDry the organic layer over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate invacuo

Sources & evidence

ORD record
ord-48bb7d2fbda7478b8573f791e3da01c1
Source dataset
uspto-grants-2001_10
Patent number
US06297259B1

Reaction notes

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