Hydrochloric Acid → 3-(7-methylimidazo[1,2-a]pyridin-2-yl)-7-(piperazin-1-yl)-2H-pyrano[3,2-c]pyridin-2-one hydrochloride

HRID 2206331Notes

Reaction equation

HRID 2206331 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([C:11]3[C:20](=[O:21])[O:19][C:18]4[CH:17]=[C:16]([N:22]5[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]5)[N:15]=[CH:14][C:13]=4[CH:12]=3)[N:10]=[C:4]2[CH:3]=1.[ClH:35]>C(Cl)Cl.O1CCOCC1>[ClH:35].[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[CH:8]=[C:9]([C:11]3[C:20](=[O:21])[O:19][C:18]4[CH:17]=[C:16]([N:22]5[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]5)[N:15]=[CH:14][C:13]=4[CH:12]=3)[N:10]=[C:4]2[CH:3]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 89783207t-butyl 4-(3-(7-methylimidazo[1,2-a]pyridin-2-yl)-2-oxo-2H-pyrano[3,2-c]pyridin-7-yl)piperazine-1-carboxylate

Product 1

HCID 897830283-(7-methylimidazo[1,2-a]pyridin-2-yl)-7-(piperazin-1-yl)-2H-pyrano[3,2-c]pyridin-2-one hydrochloride

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a suspension of t-butyl 4-(3-(7-methylimidazo[1,2-a]pyridin-2-yl)-2-oxo-2H-pyrano[3,2-c]pyridin-7-yl)piperazine-1-carboxylate (115 mg, 0.25 mmol) in CH2Cl2 (2 mL) was added 4N HCl in dioxane (1 mL). The mixture was stirred for 2 hours, and then filtered. The solid was washed with ether and dried under nitrogen to give 3-(7-methylimidazo[1,2-a]pyridin-2-yl)-7-(piperazin-1-yl)-2H-pyrano[3,2-c]pyridin-2-one hydrochloride quantitatively which was used in the next step without further purification. MS m/z 362.2 [M+H]+.

Workup

  1. filtrationfiltered
  2. washThe solid was washed with ether
  3. customdried under nitrogen

Sources & evidence

ORD record
ord-4851d03865b644a68f740d309485f829
Source dataset
uspto-grants-2016_06
Patent number
US09371336B2

Reaction notes

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