2-Chlorobenzaldehyde → HCID 131716322, compound

HRID 1199985Notes

Reaction equation

HRID 1199985 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8](=[O:18])[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:11].[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]=O.[NH2:28][C:29]([CH3:48])=[CH:30][C:31]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][N:38]1[C:46]2[CH:45]=[CH:44][N:43]=[CH:42][C:41]=2[N:40]=[C:39]1[CH3:47])=[O:32]>C(O)C>[OH2:11].[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]1[C:9]([C:8](=[O:18])[NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:28][C:29]([CH3:48])=[C:30]1[C:31]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][N:38]1[C:46]2[CH:45]=[CH:44][N:43]=[CH:42][C:41]=2[N:40]=[C:39]1[CH3:47])=[O:32].[Cl:19][C:20]1[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=1[CH:22]1[C:9]([C:8](=[O:18])[NH:7][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:28][C:29]([CH3:48])=[C:30]1[C:31]([O:33][CH2:34][CH2:35][CH2:36][CH2:37][N:38]1[C:46]2[CH:45]=[CH:44][N:43]=[CH:42][C:41]=2[N:40]=[C:39]1[CH3:47])=[O:32]

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 2680383-Oxo-3-phenyl-N-(pyridin-2-yl)propanimidic acidHCID 70357192HCID 70357192, compound

Product 1

HCID 131716322HCID 131716322, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of N-(pyrid-2-yl)-3-phenyl-3-oxopropionamide (0.84 g, 3.5 mM--see Preparation 15), 2-chlorobenzaldehyde (0.49 g, 3.5 mM) and 4-(2-methylimidazo[4,5-c]pyrid-1-yl)butyl 3-aminobut-2-enoate (1.01 g, 3.5 mM--see Preparation 13) in absolute ethanol (20 cm3) was heated at reflux, under nitrogen, for 16 hours. The cooled solution was evaporated to dryness and the residue purified by column chromatography on silica (Merck "Kieselgel 60"--Trade Mark) (2 passes) eluting primarily with ethyl acetate:diethylamine 97:3 and, secondly, dichloromethane: methanol 97:3. The product-containing fractions were evaporated to dryness, the residue re-dissolved in 2 cm3 dichloromethane, and the required solid precipitated by the addition of 25 cm3 ether, yield 0.35 g (16%), m.p. 124°-127°.

Workup

  1. temperatureat reflux, under nitrogen, for 16 hours
  2. customThe cooled solution was evaporated to dryness
  3. customthe residue purified by column chromatography on silica (Merck "Kieselgel 60"--Trade Mark) (2 passes)
  4. washeluting primarily with ethyl acetate:diethylamine 97:3
  5. customThe product-containing fractions were evaporated to dryness
  6. dissolutionthe residue re-dissolved in 2 cm3 dichloromethane
  7. customthe required solid precipitated by the addition of 25 cm3 ether, yield 0.35 g (16%), m.p. 124°-127°

Sources & evidence

ORD record
ord-acea7259ccad40e2a8f00f5aeaeba4f0
Source dataset
uspto-grants-1990_02
Patent number
US04904671

Reaction notes

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