Hydrochloric Acid → 1-[4-(6-Ethoxy-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamine

HRID 872345Notes

Reaction equation

HRID 872345 reaction equation
C(OC(=O)[NH:7][C:8]1([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[N:19]=[C:20]4[CH:25]=[CH:24][C:23]([O:26][CH2:27][CH3:28])=[CH:22][N:21]4[C:29]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:14][CH:13]=2)[CH2:11][CH2:10][CH2:9]1)(C)(C)C.Cl.O1CCOCC1>CO.C(Cl)Cl>[CH2:27]([O:26][C:23]1[CH:24]=[CH:25][C:20]2[N:21]([C:29]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)=[C:18]([C:15]3[CH:16]=[CH:17][C:12]([C:8]4([NH2:7])[CH2:9][CH2:10][CH2:11]4)=[CH:13][CH:14]=3)[N:19]=2)[CH:22]=1)[CH3:28]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 66665892{1-[4-(6-Ethoxy-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester

Product 1

HCID 666660651-[4-(6-Ethoxy-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamineYield 19%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of {1-[4-(6-ethoxy-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutyl}-carbamic acid tert-butyl ester (255 mg, 0.53 mmol) in MeOH (2.1 mL) and CH2Cl2 (3.4 mL) was added a 4 molar solution of HCl in dioxane (2.6 mL, 10.5 mmol, 20 equiv). The resulting solution was stirred at room temperature for 12 h, then was concentrated under reduced pressure. The remaining material was purified using MPLC (Isolute Flash NH2 reverse phase column; 100% CH2Cl2 for 5 min., gradient to 95% CH2Cl2: 5% MeOH over 15 minutes; gradient to 90% CH2Cl2: 10% MeOH over 15 min.; gradient to 80% CH2Cl2: 20% MeOH over 15 min.; and gradient to 75% CH2Cl2: 25% MeOH over 15 min.) to give 1-[4-(6-ethoxy-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamine (38 mg, 19%):

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe remaining material was purified
  3. wait100% CH2Cl2 for 5 min.
  4. waitgradient to 95% CH2Cl2: 5% MeOH over 15 minutes
  5. waitgradient to 90% CH2Cl2: 10% MeOH over 15 min.
  6. waitgradient to 80% CH2Cl2: 20% MeOH over 15 min.

Sources & evidence

ORD record
ord-ba28cb8e3fc4403e8c204ecab479aa16
Source dataset
uspto-grants-2015_03
Patent number
US08975265B2

Reaction notes

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