Isopropanol → HCID 178518086, compound

HRID 916255Notes

Reaction equation

HRID 916255 reaction equation
C(OC([N:11]1[CH2:15][C:14](=[CH2:16])[N:13]=[C:12]1[NH:17][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Cl:25])=O)C1C=CC=CC=1.[N:26]1[C:35]2[C:30](=[N:31][C:32](C=O)=[CH:33][CH:34]=2)[CH:29]=[CH:28][CH:27]=1.N1CCCCC1.CC([OH:47])C>>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][NH:17][C:12]1[NH:13][C:14](=[CH:16][C:32]2[CH:33]=[CH:34][C:35]3[C:30](=[CH:29][CH:28]=[CH:27][N:26]=3)[N:31]=2)[C:15](=[O:47])[N:11]=1

Participants

5

Reactant 4

HCID 3776IsopropanolHCID 8082PiperidineHCID 115863361,5-Naphthyridine-2-carbaldehydeHCID 178430741benzyl 2-[(2-chlorophenyl)methylamino]-5-methylidene-4H-imidazole-3-carboxylate

Product 1

HCID 178518086HCID 178518086, compound

Procedure

To a mixture of 2-(2-chloro-benzylamino)-4-methylene-4,5-dihydro-imidazole-1-carboxylic acid benzyl ester (62.0 mg, 0.17 mmol), 1,5-naphthyridine-6-carboxaldehyde (31.6 mg, 0.2 mmol) and iPrOH (5.0 mL) in a 25-mL round bottom flask was added piperidine (0.05 mL) and the suspension was then heated under refluxing for 3.5 hrs to give a suspension. The reaction mixture was concentrated to give a brown solid which was washed with MeOH and ether. The solid was collected by filtration to give 2-(2-chloro-benzylamino)-5-[1,5]-naphthyridin-2-ylmethylene-1,5-dihydro-imidazol-4-one as a brown solid, (10.1 mg, 16.3%). HR-ES (+) m/e calcd. for C19H14ClN5OS: (M+H)+ 364.0960. Found: 364.0959.

Workup

  1. temperaturethe suspension was then heated
  2. temperatureunder refluxing for 3.5 hrs
  3. customto give a suspension
  4. concentrationThe reaction mixture was concentrated
  5. customto give a brown solid which
  6. washwas washed with MeOH and ether
  7. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-3be96431ff5946038545072e68ca07f8
Source dataset
uspto-grants-2007_09
Patent number
US07268231B2

Reaction notes

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