Piperidine → HCID 178458706, compound

HRID 968722Notes

Reaction equation

HRID 968722 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][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=1[C:29]([F:32])([F:31])[F:30])=O)C1C=CC=CC=1.[CH:33]([C:35]1[N:36]=[C:37]2[C:42](=[CH:43][CH:44]=1)[N:41]=[CH:40][C:39]([C:45]#[N:46])=[C:38]2[O:47][CH:48]([CH3:50])[CH3:49])=O.N1CCCCC1>CC(O)C>[F:32][C:29]([F:30])([F:31])[C:20]1[CH:21]=[C:22]([C:25]([F:26])([F:28])[F:27])[CH:23]=[CH:24][C:19]=1[CH2:18][NH:17][C:12]1[NH:11][C:15](=[CH:33][C:35]2[N:36]=[C:37]3[C:42](=[CH:43][CH:44]=2)[N:41]=[CH:40][C:39]([C:45]#[N:46])=[C:38]3[O:47][CH:48]([CH3:50])[CH3:49])[C:14](=[O:16])[N:13]=1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 587243116-Formyl-4-isopropoxy-[1,5]naphthyridine-3-carbonitrileHCID 178516791benzyl 2-[[2,4-bis(trifluoromethyl)phenyl]methylamino]-5-oxo-4H-imidazole-3-carboxylate

Product 1

HCID 178458706HCID 178458706, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a mixture of 2-(2,4-bis-trifluoromethyl-benzylamino)-4-oxo-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (82.7 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 (45.6 mg, 0.19 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 6-[2-(2,4-bis-trifluoromethyl-benzylamino)-5-oxo-3,5-dihydro-imidazol-4-ylidenemethyl]-4-isopropoxy-[1,5]naphthyridine-3-carbonitrile, as a light yellow solid, 20.6 mg (20.9%). HR-ES (+) m/e calcd for C25H18F6N6O2 (M+H)+ 549.1468. found 549.1472.

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-012a3a3636c14582a85306885dba73f1
Source dataset
uspto-grants-2007_12
Patent number
US07304074B2

Reaction notes

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