Sodium Acetate → 6-[2-Amino-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-4-isobutyl-quinoline-3-carbonitrile

HRID 1297673Notes

Reaction equation

HRID 1297673 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][C:7]([C:13]#[N:14])=[C:6]2[CH2:15][CH:16]([CH3:18])[CH3:17])=O.COC1C=CC(/C=[C:34]2/[C:35]([NH:37][C:38]([S:40]/2)=[NH:39])=[O:36])=CC=1OC1CCCC1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[NH2:39][C:38]1[S:40]/[C:34](=[CH:1]\[C:3]2[CH:4]=[C:5]3[C:10](=[CH:11][CH:12]=2)[N:9]=[CH:8][C:7]([C:13]#[N:14])=[C:6]3[CH2:15][CH:16]([CH3:18])[CH3:17])/[C:35](=[O:36])[N:37]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 585858466-Formyl-4-isobutyl-quinoline-3-carbonitrileHCID 137629131(5Z)-5-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one

Product 1

HCID 116241916-[2-Amino-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-4-isobutyl-quinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Similar procedure as described in example 38 was used, starting from 6-formyl-4-isobutyl-quinoline-3-carbonitrile (example 46f), pseudothiohydantoin, sodium acetate and acetic acid to give 6-[2-amino-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-4-isobutyl-quinoline-3-carbonitrile. LC-MS m/e 337 (MH+).

Sources & evidence

ORD record
ord-af73ea8de9744c30885f430bf6e46177
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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