2-Chlorobenzaldehyde → 4-(2-Chlorophenyl)-1,4-dihydro-3-ethoxycarbonyl-6-methyl-2-[2-(2-methylimidazo[4,5-c]pyrid-1-yl)pyrid-5-yl]-5-[N-(2-pyridyl)carbamoyl]pyridine

HRID 973462Notes

Reaction equation

HRID 973462 reaction equation
[CH3:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=O)=[CH:13][N:12]=2)[C:4]2[CH:9]=[CH:8][N:7]=[CH:6][C:5]=2[N:10]=1.[NH2:25][C:26]([CH3:37])=[CH:27][C:28]([NH:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1)=[O:29].[Cl:38][C:39]1[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=1[CH:41]=O>C(O)C>[Cl:38][C:39]1[CH:46]=[CH:45][CH:44]=[CH:43][C:40]=1[CH:41]1[C:27]([C:28](=[O:29])[NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)=[C:26]([CH3:37])[NH:25][C:17]([C:14]2[CH:15]=[CH:16][C:11]([N:3]3[C:4]4[CH:9]=[CH:8][N:7]=[CH:6][C:5]=4[N:10]=[C:2]3[CH3:1])=[N:12][CH:13]=2)=[C:19]1[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

5

Reactant 3

HCID 69962-ChlorobenzaldehydeHCID 41935503-amino-N-(2-pyridyl)but-2-enamideHCID 54245582Ethyl 2-(2-methylimidazo[4,5-c]pyrid-1-yl)pyrid-5-oylacetate

Product 1

HCID 150455234-(2-Chlorophenyl)-1,4-dihydro-3-ethoxycarbonyl-6-methyl-2-[2-(2-methylimidazo[4,5-c]pyrid-1-yl)pyrid-5-yl]-5-[N-(2-pyridyl)carbamoyl]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-(2-methylimidazo[4,5-c]pyrid-1-yl)pyrid-5-oylacetate (324 mg, 1.0 mmol), 3-amino-N-(2-pyridyl)-but-2-enamide (178 mg, 1.0 mmol) and 2-chlorobenzaldehyde (140 mg, 1.0 mmol) in ethanol (4 ml) was heated under reflux for 5 hours under nitrogen. The solution was cooled and concentrated under reduced pressure. The residue was purified by flash chromatography (eluting with ethyl acetate:methanol, 6:1), followed by sonication of a suspension of the eluted product in ether/ethyl acetate, 3:1 for 45 minutes. The off-white solid product was filtered off and dried in vacuo to give the title compound, 140 mg (23%), m.p. 242°-3° C.

Workup

  1. temperatureunder reflux for 5 hours under nitrogen
  2. temperatureThe solution was cooled
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (eluting with ethyl acetate:methanol, 6:1)
  5. customfollowed by sonication of a suspension of the eluted product in ether/ethyl acetate
  6. filtrationThe off-white solid product was filtered off
  7. customdried in vacuo

Sources & evidence

ORD record
ord-ca672c9209ce44c08c89f928551b5dab
Source dataset
uspto-grants-1991_11
Patent number
US05063237

Reaction notes

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