Dichloromethane → 8-(cyclohexylmethoxy)-2-methyl-N-[(1S)-1-phenylethyl]imidazo[1,2-a]pyridine-3-carboxamide

HRID 64494Notes

Reaction equation

HRID 64494 reaction equation
[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([O:21]N4C5C=CC=CC=5N=N4)=O)=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.ClCCl.[C:34]1([C@@H:40]([NH2:42])[CH3:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl.O>[CH:1]1([CH2:7][O:8][C:9]2[C:10]3[N:11]([C:15]([C:19]([NH:42][C@H:40]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[CH3:41])=[O:21])=[C:16]([CH3:18])[N:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 758181-Phenethylamine, (-)-HCID 867135311-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}oxy)-1H-benzotriazole

Product 1

HCID 867135308-(cyclohexylmethoxy)-2-methyl-N-[(1S)-1-phenylethyl]imidazo[1,2-a]pyridine-3-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To 100 mg of 1-({[8-(cyclohexylmethoxy)-2-methylimidazo[1,2-a]pyridin-3-yl]carbonyl}oxy)-1H-benzotriazole were 1.7 ml of dichloromethane, 0.065 ml of (S)-(−)-1-phenylethylamine, and 0.07 ml of triethylamine, followed by stirring overnight. To the reaction mixture were added water and chloroform to carry out a layer separation operation, followed by drying over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography. To the obtained purified product was added diisopropyl ether, and the resulting solid was collected by filtration and dried to obtain 80 mg of 8-(cyclohexylmethoxy)-2-methyl-N-[(1S)-1-phenylethyl]imidazo[1,2-a]pyridine-3-carboxamide.

Workup

  1. customa layer separation operation
  2. dry with materialby drying over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography
  5. customTo the obtained purified product
  6. additionwas added diisopropyl ether
  7. filtrationthe resulting solid was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-72f37d169e484d5c9a85ffb7d417c82b
Source dataset
uspto-grants-2016_09
Patent number
US09447090B2

Reaction notes

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