2-Amino-4-chloropyridine → (1S)-N-Boc-1-(7-chloro-imidazo[1,2-a]pyridin-2-yl)-3-methyl-butylamine

HRID 2094343Notes

Reaction equation

HRID 2094343 reaction equation
Cl[CH2:2][C:3]([CH:5]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:6][CH:7]([CH3:9])[CH3:8])=O.[NH2:18][C:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][N:20]=1>CO>[C:11]([NH:10][C@H:5]([C:3]1[N:18]=[C:19]2[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][N:20]2[CH:2]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:17]

Participants

4

Reactant 2

HCID 5818662-Amino-4-chloropyridineHCID 13727771Boc-Leu-CMK

Product 1

HCID 86652239(1S)-N-Boc-1-(7-chloro-imidazo[1,2-a]pyridin-2-yl)-3-methyl-butylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.68 g (6.37 mmol) tert.-butyl [1-(2-chloro-acetyl)-3-methyl-butyl]-carbamate in 15 ml of methanol are combined with 819 mg (6.37 mmol) 2-amino-4-chloro-pyridine at ambient temperature with stirring and the mixture is refluxed for 3 days. After evaporation i. vac. the residue is combined with 5% sodium hydrogen carbonate solution and stirred for 20 h at ambient temperature. Then it is extracted with dichloromethane, the combined organic phases are dried over sodium sulphate and evaporated down completely i. vac. The residue is purified by chromatography on silica gel (eluting gradient: dichloromethane/ethanol=100:0->94:6).

Workup

  1. temperaturethe mixture is refluxed for 3 days
  2. customAfter evaporation i
  3. stirringstirred for 20 h at ambient temperature
  4. extractionThen it is extracted with dichloromethane
  5. dry with materialthe combined organic phases are dried over sodium sulphate
  6. customevaporated down completely
  7. customThe residue is purified by chromatography on silica gel (eluting gradient: dichloromethane/ethanol=100:0->94:6)

Sources & evidence

ORD record
ord-b1cd5429812c4fa5accc3cc5230a7aef
Source dataset
uspto-grants-2013_05
Patent number
US08445525B2

Reaction notes

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