Hydrochloric Acid → 1-(piperidin-3-yl)-1H-imidazo[4,5-c]pyridin-6-amine hydrochloride

HRID 919647Notes

Reaction equation

HRID 919647 reaction equation
C1(C(=[N:14][C:15]2[N:20]=[CH:19][C:18]3[N:21]=[CH:22][N:23]([CH:24]4[CH2:29][CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]4)[C:17]=3[CH:16]=2)C2C=CC=CC=2)C=CC=CC=1.[ClH:37]>C1COCC1>[ClH:37].[NH:26]1[CH2:27][CH2:28][CH2:29][CH:24]([N:23]2[C:17]3[CH:16]=[C:15]([NH2:14])[N:20]=[CH:19][C:18]=3[N:21]=[CH:22]2)[CH2:25]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 87946249tert-butyl 3-(6-((diphenylmethylene)amino)-1H-imidazo[4,5-c]pyridin-1-yl)piperidine-1-carboxylate

Product 1

HCID 675171261-(piperidin-3-yl)-1H-imidazo[4,5-c]pyridin-6-amine hydrochlorideYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 3-(6-((diphenylmethylene)amino)-1H-imidazo[4,5-c]pyridin-1-yl)piperidine-1-carboxylate (400 mg, 0.83 mmol, 1.0 eq) in THF (4 mL) was added HCl (4 N solution in 1,4 dioxane, 4 mL). The mixture was stirred at rt for 3 h and concentrated in vacuo to afford a residue which was washed with EtOAc (10 mL×3) to give crude title compound (180 mg, 95%) as brown solid. 1H NMR (400 MHz, DMSO-d6) δ: 9.82 (s, 1H), 8.73-8.65 (m, 1H), 7.74-7.70 (m, 1H), 7.58-7.56 (m, 1H), 4.04-4.02 (m, 1H), 3.67-3.66 (m, 0.5H), 3.48-3.32 (m, 2H), 2.95-2.79 (m, 1.5H), 2.18 (s, 1H), 1.99-1.96 (m, 3H), 1.75-1.73 (m, 1H). ESI-MS (M+H+): 218.0.

Workup

  1. concentrationconcentrated in vacuo
  2. customto afford a residue which
  3. washwas washed with EtOAc (10 mL×3)

Sources & evidence

ORD record
ord-29ecdd7c2200425c989ba4c69a069d0a
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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