4-Ethoxy-3-methoxyphenethylamine → 2-{[2-(4-Ethoxy-3-methoxyphenyl)ethyl]amino}ethyl[5-methyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]amine

HRID 1634558Notes

Reaction equation

HRID 1634558 reaction equation
Cl[CH2:2][CH2:3][NH:4][C:5]1[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]2[N:12]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[CH:13]=[N:14][C:6]=12.[CH2:24]([O:26][C:27]1[CH:35]=[CH:34][C:30]([CH2:31][CH2:32][NH2:33])=[CH:29][C:28]=1[O:36][CH3:37])[CH3:25]>CN1C(=O)CCC1>[CH2:24]([O:26][C:27]1[CH:35]=[CH:34][C:30]([CH2:31][CH2:32][NH:33][CH2:2][CH2:3][NH:4][C:5]2[CH:10]=[C:9]([CH3:11])[N:8]=[C:7]3[N:12]([C:15]4[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=4[CH3:23])[CH:13]=[N:14][C:6]=23)=[CH:29][C:28]=1[O:36][CH3:37])[CH3:25]

Participants

4

Reactant 2

HCID 1420764-Ethoxy-3-methoxyphenethylamineHCID 22034143(2-Chloroethyl)[5-methyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]-amine

Product 1

HCID 220341372-{[2-(4-Ethoxy-3-methoxyphenyl)ethyl]amino}ethyl[5-methyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]amine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Heat a solution of (2-chloroethyl)[5-methyl-3-(2,4,6,-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl]-amine (0.030 g, 0.09 mmol) and 4-ethoxy-3-methoxy phenethylamine (0.10 g, 0.55 mmol) in dry NMP (2 mL) at 110° C. for 16 h. Pour the cooled mixture onto water (20 mL) and extract twice with EtOAc (20 mL). Wash the combined extracts with brine (30 mL), dry, and evaporate in vacuo. Purify by flash column chromatography (10% MeOH in CH2Cl2 with 0.1% ammonium hydroxide) to obtain the title compound as a solid.

Workup

  1. additionPour the cooled mixture onto water (20 mL)
  2. extractionextract twice with EtOAc (20 mL)
  3. washWash the combined extracts with brine (30 mL)
  4. customdry
  5. customevaporate in vacuo
  6. customPurify by flash column chromatography (10% MeOH in CH2Cl2 with 0.1% ammonium hydroxide)

Sources & evidence

ORD record
ord-3ebb126b6da345c494693506c8209413
Source dataset
uspto-grants-2003_01
Patent number
US06506762B1

Reaction notes

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