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 1792269Notes

Reaction equation

HRID 1792269 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-e1c295b6c13a4b0693de6ccd9488b432
Source dataset
uspto-grants-2006_07
Patent number
US07074929B2

Reaction notes

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