Hydrochloric Acid → 6-[2-Amino-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-4-(piperidin-4-yloxy)-quinoline-3-carbonitrile hydrochloride

HRID 1297655Notes

Reaction equation

HRID 1297655 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][C:16]=2[C:33]#[N:34])[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:35]>O1CCOCC1>[ClH:35].[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][C:16]([C:33]#[N:34])=[C:15]3[O:14][CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)/[C:27](=[O:32])[N:28]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 116559284-{6-[2-Amino-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-3-cyano-quinolin-4-yloxy}-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 1317265406-[2-Amino-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-4-(piperidin-4-yloxy)-quinoline-3-carbonitrile hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 4-{6-[2-amino-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-3-cyano-quinolin-4-yloxy}-piperidine-1-carboxylic acid tert-butyl ester (example 29, 34 mg, 0.071 mmol) was added 4N HCl in dioxane (3 mL). After stirring 30 min and removal of the solvent, ether was added. The solid was collected by filtration and washed with ether and dried to give 6-[2-amino-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-4-(piperidin-4-yloxy)-quinoline-3-carbonitrile hydrochloride. LC-MS m/e 480 (MH+).

Workup

  1. customremoval of the solvent, ether
  2. additionwas added
  3. filtrationThe solid was collected by filtration
  4. washwashed with ether
  5. customdried

Sources & evidence

ORD record
ord-1b27db3020754d1dbccc6112c98e9028
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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