(S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamine → HCID 178427145, compound

HRID 551174Notes

Reaction equation

HRID 551174 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[CH2:17][CH2:16][CH2:15][N:14]([CH3:18])[CH2:13][CH2:12]1)[C:5](Cl)=[O:6].[Cl:19][C:20]1[CH:31]=[CH:30][C:23]2[NH:24][C:25]([C@@H:27]([NH2:29])[CH3:28])=[N:26][C:22]=2[CH:21]=1>C1COCC1>[Cl:19][C:20]1[CH:31]=[CH:30][C:23]2[NH:24][C:25]([C@@H:27]([NH:29][C:5](=[O:6])[C:4]3[CH:8]=[CH:9][C:10]([N:11]4[CH2:17][CH2:16][CH2:15][N:14]([CH3:18])[CH2:13][CH2:12]4)=[C:2]([CH3:1])[CH:3]=3)[CH3:28])=[N:26][C:22]=2[CH:21]=1

Participants

4

Reactant 2

HCID 42034613(S)-1-(5-chloro-1H-benzimidazol-2-yl)ethylamineHCID 872489583-methyl-4-(4-N-methyl-[1,4]diazepan-1-yl)-benzoic acid chloride

Product 1

HCID 178427145HCID 178427145, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

489 mg (1.61 mmol) 3-methyl-4-(4-N-methyl-[1,4]diazepan-1-yl)-benzoic acid chloride are placed together with 400 mg (3.96 mmol) TEA in 10 ml THF at ambient temperature and a solution of 433 mg (1.61 mmol) (1S)-1-(5-chloro-1H-benzimidazol-2-yl)-ethylamine is added dropwise with stirring. After 16 hours stirring at ambient temperature the mixture is evaporated down i. vac., the residue is combined with water and extracted with ethyl acetate. The combined organic phases are washed with sat. sodium chloride solution, dried over sodium sulphate and evaporated down i. vac. The residue is purified by chromatography on aluminium oxide (eluant: dichloromethane/methanol 100:1). The fractions evaporated down are treated with ethereal hydrochloric acid, after total concentration evaporated twice with ethyl acetate and diethyl ether and dried i. vac. at 70° C.

Workup

  1. stirringAfter 16 hours stirring at ambient temperature the mixture
  2. customis evaporated down i
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases are washed with sat. sodium chloride solution
  5. dry with materialdried over sodium sulphate
  6. customevaporated down i
  7. customThe residue is purified by chromatography on aluminium oxide (eluant: dichloromethane/methanol 100:1)
  8. customThe fractions evaporated down
  9. additionare treated with ethereal hydrochloric acid
  10. concentrationafter total concentration
  11. customevaporated twice with ethyl acetate and diethyl ether
  12. customdried i
  13. customat 70° C.

Sources & evidence

ORD record
ord-7cc79c2205d54aa98ce401f3a7fbcd3e
Source dataset
uspto-grants-2011_05
Patent number
US07947700B2

Reaction notes

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