4(5H)-Thiazolone, 2-amino- → 4-{6-[2-Amino-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-quinolin-4-yloxy}-piperidine-1-carboxylic acid tert-butyl ester

HRID 853032Notes

Reaction equation

HRID 853032 reaction equation
[C:1]([O:5][C:6]([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]=O)[CH:23]=3)[N:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:27][C:28]1[S:29][CH2:30][C:31](=[O:33])[N:32]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[C:1]([O:5][C:6]([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:30]4/[C:31](=[O:33])[N:32]=[C:28]([NH2:27])[S:29]/4)[CH:23]=3)[N:18]=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 111754(5H)-Thiazolone, 2-amino-HCID 517045Sodium AcetateHCID 58615384HCID 58615384, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The similar procedure as described in example 35 was used, starting from 4-(6-formyl-quinolin-4-yloxy)-piperidine-1-carboxylic acid tert-butyl ester, 2-Amino-thiazol-4-one (example 48b), sodium acetate and acetic acid to obtain 4-{6-[2-amino-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-quinolin-4-yloxy}-piperidine-1-carboxylic acid tert-butyl ester as a yellow solid. Purification was performed with flash chromatography (Merck silica gel 60, 230-400 mesh, 1%-5% methanol in dichloromethane for 30 min. LC-MS m/e 455.5 (MH+).

Sources & evidence

ORD record
ord-62f8d3b4bb46415eb2705c1b86e0540b
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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