Hydrochloric Acid → {4-[3-(4-Aminomethyl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-phenyl}-(4-methyl-piperazin-1-yl)-methanone, bis hydrochloride

HRID 1446726Notes

Reaction equation

HRID 1446726 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([C:24]4[CH:29]=[CH:28][C:27]([C:30]([N:32]5[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]5)=[O:31])=[CH:26][CH:25]=4)=[CH:23][C:18]3=[N:17][CH:16]=2)=[CH:11][CH:10]=1)(C)(C)C.[ClH:40]>O1CCOCC1>[ClH:40].[ClH:40].[NH2:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:15]2[N:19]3[CH:20]=[CH:21][C:22]([C:24]4[CH:25]=[CH:26][C:27]([C:30]([N:32]5[CH2:37][CH2:36][N:35]([CH3:38])[CH2:34][CH2:33]5)=[O:31])=[CH:28][CH:29]=4)=[CH:23][C:18]3=[N:17][CH:16]=2)=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68543678(4-{7-[4-(4-Methyl-piperazine-1-carbonyl)-phenyl]-imidazo[1,2-a]pyridin-3-yl}-benzyl)-carbamic acid tert-butyl ester

Product 1

HCID 131727906{4-[3-(4-Aminomethyl-phenyl)-imidazo[1,2-a]pyridin-7-yl]-phenyl}-(4-methyl-piperazin-1-yl)-methanone, bis hydrochlorideYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

Combine (4-{7-[4-(4-methyl-piperazine-1-carbonyl)-phenyl]-imidazo[1,2-a]pyridin-3-yl}-benzyl)-carbamic acid tert-butyl ester (0.87 g, 1.65 mmol), 4N HCl in 1,4-dioxane (15 mL, 60 mmol) in 1,4-dioxane (35 mL) and stir overnight (16 hours). Concentrate slurry to a residue. Dissolve residue in methanol (50 mL) and concentrate to afford the title compound (0.90 g, 100%). MS(ES), m/z 426 (M+1 for free base).

Workup

  1. concentrationConcentrate slurry to a residue
  2. concentrationDissolve residue in methanol (50 mL) and concentrate

Sources & evidence

ORD record
ord-2d6510960de64a55918d3e279698624b
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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