Hydrochloric Acid → 2-Amino-5-[1-[4-(piperidin-4-yloxy)-quinolin-6-yl]-meth-(z)-ylidene]-thiazol-4-one

HRID 853033Notes

Reaction equation

HRID 853033 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22](/[CH:25]=[C:26]4/[C:27](=[O:32])[N:28]=[C:29]([NH2:31])[S:30]/4)[CH:23]=3)[N:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>ClCCl>[NH2:31][C:29]1[S:30]/[C:26](=[CH:25]\[C:22]2[CH:23]=[C:24]3[C:19](=[CH:20][CH:21]=2)[N:18]=[CH:17][CH:16]=[C:15]3[O:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)/[C:27](=[O:32])[N:28]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 586153684-{6-[2-Amino-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-quinolin-4-yloxy}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 586153782-Amino-5-[1-[4-(piperidin-4-yloxy)-quinolin-6-yl]-meth-(z)-ylidene]-thiazol-4-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The suspension of 4-{6-[2-amino-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-quinolin-4-yloxy}-piperidine-1-carboxylic acid tert-butyl ester (70 mg, 0.15 mmol) in dichloromethane (1 ml) was treated with hydrogen chloride (in 1,4-dioxane, 4M, 1 ml) for 1.5 hr at room temperature. After removing the solvent, the obtained solid was treated with either. Ion exchange extraction chromatography (Cation exchanger: benenesulfonic acid, 2 g/6 ml, 1M ammonia in methanol and dichloromethane) afforded the free base form of 2-Amino-5-[1-[4-(piperidin-4-yloxy)-quinolin-6-yl]-meth-(Z)-ylidene]-thiazol-4-one. LC-MS m/e 355 (MH+).

Workup

  1. customAfter removing the solvent
  2. additionthe obtained solid was treated with either
  3. extractionIon exchange extraction chromatography (Cation exchanger: benenesulfonic acid, 2 g/6 ml, 1M ammonia in methanol and dichloromethane)

Sources & evidence

ORD record
ord-fb3e1f5548ea47bea880094618f98b02
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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