Ethylenediamine → (2-Aminoethyl)[2-methyl-9-(2,4,6-trimethylphenyl)-pyridino[2,3-b]indolizin-4-yl]amine

HRID 2121584Notes

Reaction equation

HRID 2121584 reaction equation
Cl[C:2]1[C:14]2[N:13]3[C:8]([C:9]([C:15]4[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=4[CH3:23])=[CH:10][CH:11]=[CH:12]3)=[CH:7][C:6]=2[N:5]=[C:4]([CH3:24])[CH:3]=1.[CH2:25]([NH2:28])[CH2:26][NH2:27]>CN1C(=O)CCC1>[NH2:27][CH2:26][CH2:25][NH:28][C:2]1[C:14]2[N:13]3[C:8]([C:9]([C:15]4[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=4[CH3:23])=[CH:10][CH:11]=[CH:12]3)=[CH:7][C:6]=2[N:5]=[C:4]([CH3:24])[CH:3]=1

Participants

4

Reactant 2

HCID 3301EthylenediamineHCID 69661784HCID 69661784, compound

Product 1

HCID 69661982(2-Aminoethyl)[2-methyl-9-(2,4,6-trimethylphenyl)-pyridino[2,3-b]indolizin-4-yl]amine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Heat a solution of 4-chloro-2-methyl-9-(2,4,6-trimethylphenyl)pyridino[2,3-b]-indolizine (0.35 g, 1.04 mmol), and ethylene diamine (0.32 g, 1.04 mmol) in dry NMP (3 mL) at 100° C. for 5 h. Pour the cooled mixture onto water (30 mL) and extract twice with EtOAc (30 mL). Wash the combined extract with brine (30 mL), dry, and evaporate in vacuo. Purify by preparative TLC (20% MeOH in CH2Cl2 with 1% ammonium hydroxide) to obtain the title compound as a colorless oil.

Workup

  1. additionPour the cooled mixture onto water (30 mL)
  2. extractionextract twice with EtOAc (30 mL)
  3. washWash the
  4. extractioncombined extract with brine (30 mL)
  5. customdry
  6. customevaporate in vacuo
  7. customPurify by preparative TLC (20% MeOH in CH2Cl2 with 1% ammonium hydroxide)

Sources & evidence

ORD record
ord-411ada6248f04031b6986b7e1bb5cc1d
Source dataset
uspto-grants-2004_02
Patent number
US06696445B2

Reaction notes

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