Cyclohexylamine → [2,5-Dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl][2-(cyclohexylamino)ethyl]amine

HRID 1634561Notes

Reaction equation

HRID 1634561 reaction equation
[CH3:1][C:2]1[N:3]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])[C:4]2[C:9]([N:10]=1)=[C:8]([NH:11][CH2:12][CH2:13]Cl)[CH:7]=[C:6]([CH3:15])[N:5]=2.[CH:25]1([NH2:31])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>CN1C(=O)CCC1>[CH3:1][C:2]1[N:3]([C:16]2[C:21]([CH3:22])=[CH:20][C:19]([CH3:23])=[CH:18][C:17]=2[CH3:24])[C:4]2[C:9]([N:10]=1)=[C:8]([NH:11][CH2:12][CH2:13][NH:31][CH:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1)[CH:7]=[C:6]([CH3:15])[N:5]=2

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 22034113[2,5-Dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl](2-chloroethyl)amine

Product 1

HCID 22034117[2,5-Dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl][2-(cyclohexylamino)ethyl]amine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Heat a solution of [2,5-dimethyl-3-(2,4,6-trimethylphenyl)imidazolo[5,4-b]pyridin-7-yl](2-chloroethyl)amine (0.04 g, 0.12 mmol), and cyclohexyl amine (0.13 mL g, 1.16 mmol) in dry NMP (2 mL) at 80° C. for 20 h. Pour the cooled mixture onto water (20 mL) and extract twice with ethyl acetate (20 mL). Wash the combined extracts with brine (20 mL), dry, and evaporate in vacuo. Purify by flash column chromatography (10% methanol in CH2Cl2 with 0.1% ammonium hydroxide) to obtain the title compound as a white solid.

Workup

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

Sources & evidence

ORD record
ord-ce973250e6f3424e9f0d99b7584a80e3
Source dataset
uspto-grants-2003_01
Patent number
US06506762B1

Reaction notes

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