Piperidine → HCID 178458705, compound

HRID 968723Notes

Reaction equation

HRID 968723 reaction equation
C(OC([N:11]1[CH2:15][C:14](=[O:16])[N:13]=[C:12]1[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([F:28])([F:27])[F:26])=O)C1C=CC=CC=1.[CH:29]([C:31]1[N:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[N:37]=[CH:36][C:35]([C:41]#[N:42])=[C:34]2[O:43][CH:44]([CH3:46])[CH3:45])=O.N1CCCCC1>CC(O)C>[CH:44]([O:43][C:34]1[C:33]2[C:38](=[CH:39][CH:40]=[C:31]([CH:29]=[C:15]3[C:14](=[O:16])[N:13]=[C:12]([NH:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=4[C:25]([F:26])([F:27])[F:28])[NH:11]3)[N:32]=2)[N:37]=[CH:36][C:35]=1[C:41]#[N:42])([CH3:46])[CH3:45]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 587243116-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrileHCID 178516790benzyl 5-oxo-2-[[2-(trifluoromethyl)phenyl]methylamino]-4H-imidazole-3-carboxylate

Product 1

HCID 178458705HCID 178458705, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 4-oxo-2-(2-trifluoromethyl-benzylamino)-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (70.4 mg, 0.18 mmol) (prepared as described in C-H Kwon et al. J. Med. Chem. 1991, 34, 1845-1849), 6-formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile (56.5 mg, 0.23 mmol) (see Example 1) and iPrOH (5 mL) in a 25-mL round bottom flask was added piperidine (0.05 mL) and the suspension was then heated under refluxing for 5 h to give a brown solution. The reaction mixture was cooled to r.t. and concentrated to give a light yellow solid, 66.3 mg, which was purified by flash column purification to give 4-isopropoxy-6-[5-oxo-2-(2-trifluoromethyl-benzylamino)-3,5-dihydro-imidazol-4-ylidenemethyl]-[1,5]naphthyridine-3-carbonitrile, as a light yellow solid, 18.6 mg (21.5%). HR-ES (+) m/e calcd for C24H19F3N6O2 (M+H)+ 481.1595. found 481.1595.

Workup

  1. temperaturethe suspension was then heated
  2. temperatureunder refluxing for 5 h
  3. customto give a brown solution
  4. concentrationconcentrated
  5. customto give a light yellow solid, 66.3 mg, which
  6. customwas purified by flash column purification

Sources & evidence

ORD record
ord-2e38aa8007b74776b5f628c35949af03
Source dataset
uspto-grants-2007_12
Patent number
US07304074B2

Reaction notes

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