2-(N-Benzyl-N-methylamino)ethyl 3-amino-2-butenoate → Methyl 2-(N-benzyl-N-methylamino)ethyl 2,6-dimethyl-4-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate

HRID 1650153Notes

Reaction equation

HRID 1650153 reaction equation
[C:1]([C:4](=[CH:9][C:10]1[C:11]([CH3:19])=[N:12][N:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=12)[C:5]([O:7][CH3:8])=[O:6])(=O)[CH3:2].[NH2:20]/[C:21](/[CH3:37])=[CH:22]\[C:23]([O:25][CH2:26][CH2:27][N:28]([CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH3:29])=[O:24]>C(O)(C)C>[CH3:2][C:1]1[NH:20][C:21]([CH3:37])=[C:22]([C:23]([O:25][CH2:26][CH2:27][N:28]([CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH3:29])=[O:24])[CH:9]([C:10]2[C:11]([CH3:19])=[N:12][N:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=23)[C:4]=1[C:5]([O:7][CH3:8])=[O:6]

Participants

4

Reactant 2

HCID 125291882-(N-Benzyl-N-methylamino)ethyl 3-amino-2-butenoateHCID 54466336Methyl 2-acetyl-3-(2-methylpyrazolo[1,5-a]pyridin-3-yl)acrylate

Product 1

HCID 14303276Methyl 2-(N-benzyl-N-methylamino)ethyl 2,6-dimethyl-4-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of 24.9 g of methyl 2-acetyl-3-(2-methylpyrazolo[1,5-a]pyridin-3-yl)acrylate and 28.8 g of 2-(N-benzyl-N-methylamino)ethyl 3-aminocrotonate in 125 ml of isopropylalcohol was refluxed for 8.5 hours, then concentrated. The resulting residue was dissolved in 100 ml of ethyl acetate, washed with 1 N-hydrochloric acid, and then extracted with 2 N-hydrochloric acid three times. The resulting hydrochloric acid layer was alkalized with 5 N-aqueous sodium hydroxide at pH 9, and then extracted with ethyl acetate. The ethyl acetate layer was washed with salt water, dried over anhydrous sodium sulfate and then concentrated. Hexane was added to the resulting residue, and insoluble layer was collected, then recrystallized from diethyl ether-hexane mixtures.

Workup

  1. concentrationconcentrated
  2. dissolutionThe resulting residue was dissolved in 100 ml of ethyl acetate
  3. washwashed with 1 N-hydrochloric acid
  4. extractionextracted with 2 N-hydrochloric acid three times
  5. extractionextracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with salt water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated
  9. additionHexane was added to the resulting residue, and insoluble layer
  10. customwas collected
  11. customrecrystallized from diethyl ether-hexane mixtures

Sources & evidence

ORD record
ord-dfb251c477ab43eb8951ce621780bfe0
Source dataset
uspto-grants-1990_05
Patent number
US04923871

Reaction notes

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