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

HRID 1297723Notes

Reaction equation

HRID 1297723 reaction equation
[CH3:1][C:2]([CH3:20])([CH3:19])[CH2:3][O:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH:15]=O)[CH:13]=2)[N:8]=[CH:7][C:6]=1[C:17]#[N:18].COC1C=CC(/C=[C:36]2/[C:37]([NH:39][C:40]([S:42]/2)=[NH:41])=[O:38])=CC=1OC1CCCC1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[NH2:41][C:40]1[S:42]/[C:36](=[CH:15]\[C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][C:6]([C:17]#[N:18])=[C:5]3[O:4][CH2:3][C:2]([CH3:20])([CH3:19])[CH3:1])/[C:37](=[O:38])[N:39]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 585858714-(2,2-Dimethyl-propoxy)-6-formyl-quinoline-3-carbonitrileHCID 137629131(5Z)-5-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one

Product 1

HCID 116030606-[2-Amino-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-4-(2,2-dimethyl-propoxy)-quinoline-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Similar procedure as described in example 28c was used, starting from 4-(2,2-dimethyl-propoxy)-6-formyl-quinoline-3-carbonitrile (example 67b), pseudothiohydantoin, sodium acetate and acetic acid to give 6-[2-amino-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-4-(2,2-dimethyl-propoxy)-quinoline-3-carbonitrile. LC-MS m/e 367 (MH+).

Sources & evidence

ORD record
ord-83a1f5bf178a4f699bc62168fff03f12
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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