Cyclopentylamine → HCID 22034122, compound

HRID 2121607Notes

Reaction equation

HRID 2121607 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2=[N:14][C:15]([CH3:22])=[CH:16][C:17]([NH:18][CH2:19][CH2:20]Cl)=[C:12]2[N:11]=[C:10]1[CH3:23].[CH:24]1([NH2:29])[CH2:28][CH2:27][CH2:26][CH2:25]1>CN1C(=O)CCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:13]2=[N:14][C:15]([CH3:22])=[CH:16][C:17]([NH:18][CH2:19][CH2:20][NH:29][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)=[C:12]2[N:11]=[C:10]1[CH3:23]

Participants

4

Reactant 2

HCID 2906CyclopentylamineHCID 22034141HCID 22034141, compound

Product 1

HCID 22034122HCID 22034122, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

Heat a solution of [3-(2,4-dichlorophenyl)-2,5-dimethylimidazolo[5,4-b]pyridin-7-yl](2-chloroethyl)amine (0.08 g, 0.22 mmol), and cyclopentyl amine (0.2 mL g, 0.22 mmol) in dry NMP (3 mL) at 80° C. for 20 h. Pour the cooled mixture onto water (30 mL) and extract twice with EtOAc (50 mL). Wash the combined extracts with brine (50 mL), dry, and evaporate in vacuo. Purify by preparative TLC (10% MeOH in CH2Cl2) to obtain the title compound as a yellow oil.

Workup

  1. additionPour the cooled mixture onto water (30 mL)
  2. extractionextract twice with EtOAc (50 mL)
  3. washWash the combined extracts with brine (50 mL)
  4. customdry
  5. customevaporate in vacuo
  6. customPurify by preparative TLC (10% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-5e4f42d4f84f4d2dbbd35213bf931cff
Source dataset
uspto-grants-2004_02
Patent number
US06696445B2

Reaction notes

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