Sodium Acetate → 4-{6-[2-Amino-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-3-cyano-quinolin-4-yloxy}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1297654Notes

Reaction equation

HRID 1297654 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](C=O)[CH:23]=3)[N:18]=[CH:17][C:16]=2[C:27]#[N:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].COC1C=CC(/[CH:43]=[C:44]2/[C:45]([NH:47][C:48]([S:50]/2)=[NH:49])=[O:46])=CC=1OC1CCCC1.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:43]=[C:44]4/[C:45](=[O:46])[N:47]=[C:48]([NH2:49])[S:50]/4)[CH:23]=3)[N:18]=[CH:17][C:16]=2[C:27]#[N:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 585858404-(3-Cyano-6-formyl-quinolin-4-yloxy)-piperidine-1-carboxylic acid tert-butyl esterHCID 137629131(5Z)-5-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Similar procedure as described in example 28c was used, starting from 4-(3-cyano-6-formyl-quinolin-4-yloxy)-piperidine-1-carboxylic acid tert-butyl ester, pseudothiohydantoin, sodium acetate and acetic acid to give 4-{6-[2-amino-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-3-cyano-quinolin-4-yloxy}-piperidine-1-carboxylic acid tert-butyl ester. LC-MS m/e 480 (MH+).

Sources & evidence

ORD record
ord-ef4fd678824047449d8f45362e65e9e0
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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