Dimethylethylamine → (2-{[2-(4-Ethoxy-3-methoxyphenyl)ethyl]amino}ethyl)[2-methyl-9-(2,4,6-trimethylphenyl)pyridino[2,3-b]indolizin-4-yl]amine

HRID 1634545Notes

Reaction equation

HRID 1634545 reaction equation
[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([NH:13][CH2:14][CH2:15][NH:16][C:17]2[C:29]3[N:28]4[C:23]([C:24]([C:30]5[C:35]([CH3:36])=[CH:34][C:33]([CH3:37])=[CH:32][C:31]=5[CH3:38])=[CH:25][CH:26]=[CH:27]4)=[CH:22][C:21]=3[N:20]=[C:19]([CH3:39])[CH:18]=2)=O)=[CH:6][C:5]=1[O:40][CH3:41])[CH3:2].[AlH3].N(CC)(C)C>C1COCC1>[CH2:1]([O:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][NH:13][CH2:14][CH2:15][NH:16][C:17]2[C:29]3[N:28]4[C:23]([C:24]([C:30]5[C:31]([CH3:38])=[CH:32][C:33]([CH3:37])=[CH:34][C:35]=5[CH3:36])=[CH:25][CH:26]=[CH:27]4)=[CH:22][C:21]=3[N:20]=[C:19]([CH3:39])[CH:18]=2)=[CH:6][C:5]=1[O:40][CH3:41])[CH3:2]

Participants

5

Reactant 3

HCID 11723DimethylethylamineHCID 14488Aluminum hydrideHCID 696624812-(4-ethoxy-3-methoxy-phenyl)-N-{2-[2-methyl-9-(2,4,6-trimethyl-phenyl)-pyridino[2,3-b]indolizin-4-ylamino]-ethyl}-acetamide

Product 1

HCID 69662626(2-{[2-(4-Ethoxy-3-methoxyphenyl)ethyl]amino}ethyl)[2-methyl-9-(2,4,6-trimethylphenyl)pyridino[2,3-b]indolizin-4-yl]amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Treat a solution of 2-(4-ethoxy-3-methoxy-phenyl)-N-{2-[2-methyl-9-(2,4,6-trimethyl-phenyl)-pyridino[2,3-b]indolizin-4-ylamino]-ethyl}-acetamide (0.08 g, 0.145 mmol) in THF (5 mL) with AlH3.NMe2Et (3 mL, 1.45 mmol) and heat to reflux for 14 h. Cool the resulting mixture ambient temperature, quench with Na2CO3, 10H2O (0.3 g) and stir at ambient temperature for 15 min. Filter the solution through Celite and wash with several portions of CH2Cl2. Concentrate the filtrate in vacuo to dryness and purify preparative TLC (10% MeOH in CH2C2 with 0.5% ammonium hydroxide) to the title compound as a solid,

Workup

  1. temperatureto reflux for 14 h
  2. customquench with Na2CO3, 10H2O (0.3 g)
  3. filtrationFilter the solution through Celite
  4. washwash with several portions of CH2Cl2
  5. concentrationConcentrate the filtrate in vacuo to dryness
  6. custompurify preparative TLC (10% MeOH in CH2C2 with 0.5% ammonium hydroxide) to the title compound as a solid

Sources & evidence

ORD record
ord-e167226ebe554b2caa7ae0125f35e87b
Source dataset
uspto-grants-2003_01
Patent number
US06506762B1

Reaction notes

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