1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 178438741, compound

HRID 1412495Notes

Reaction equation

HRID 1412495 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([NH:7][CH:8]2[CH2:11][CH:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:9]2)=[N:5][N:6]=1.[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[CH:30]=[CH:29][C:28]([CH2:31][CH:32]([C:38](=O)[CH2:39][CH2:40][CH3:41])[C:33](OCC)=[O:34])=[C:27]([F:43])[CH:26]=1)#[N:18].N12CCCN=C1CCCCC2>C(N(CC)C1C=CC=CC=1)C.C(OCC)(=O)C>[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]2[C:33](=[O:34])[N:7]([C@H:8]3[CH2:9][C@H:10]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:11]3)[C:4]3[N:5]([N:6]=[C:2]([CH3:1])[N:3]=3)[C:38]=2[CH2:39][CH2:40][CH3:41])=[C:27]([F:43])[CH:26]=1)#[N:18]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57460949Ethyl 2-[(2'-cyano-3-fluorobiphenyl-4-yl)methyl]-3-oxohexanoateHCID 178469196HCID 178469196, compound

Product 1

HCID 178438741HCID 178438741, compound

Reagents, catalysts & solvents 2

HCID 7061N,N-DiethylanilineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 3-[(5-methyl-4H-1,2,4-triazol-3-yl)amino]cyclobutanecarboxylate (7.85 g), ethyl 2-[(2′-cyano-3-fluorobiphenyl-4-yl)methyl]-3-oxohexanoate (23.15 g) and 1,8-diazabicyclo[5.4.0]undec-7-ene (2.62 mL) in N,N-diethylaniline (70 mL) was stirred at 180° C. for 20 hr. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with 1 N hydrochloric acid and then with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=85/15→65/35 (volume ratio)] to give the title compound as a pale-yellow amorphous compound (1.89 g, 10%).

Workup

  1. washthe mixture was washed with 1 N hydrochloric acid
  2. dry with materialwith saturated brine, and dried over anhydrous magnesium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was purified by silica gel chromatography [eluent: hexane/ethyl acetate=85/15→65/35 (volume ratio)]

Sources & evidence

ORD record
ord-a4a9715a97344017a0eba54f675407ae
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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