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

HRID 1297635Notes

Reaction equation

HRID 1297635 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]=O)[CH:12]=2)[N:7]=[CH:6][C:5]=1[C:16]#[N:17])[CH3:2].COC1C=CC(/C=[C:33]2/[C:34]([NH:36][C:37]([S:39]/2)=[NH:38])=[O:35])=CC=1OC1CCCC1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[NH2:38][C:37]1[S:39]/[C:33](=[CH:14]\[C:11]2[CH:12]=[C:13]3[C:8](=[CH:9][CH:10]=2)[N:7]=[CH:6][C:5]([C:16]#[N:17])=[C:4]3[O:3][CH2:1][CH3:2])/[C:34](=[O:35])[N:36]=1

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 585858184-Ethoxy-6-formyl-quinoline-3-carbonitrileHCID 137629131(5Z)-5-[(3-cyclopentyloxy-4-methoxyphenyl)methylidene]-2-imino-1,3-thiazolidin-4-one

Product 1

HCID 115949886-[2-Amino-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-4-ethoxy-quinoline-3-carbonitrileYield 47%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
110 °C

Procedure

To the suspension of 4-ethoxy-6-formyl-quinoline-3-carbonitrile (example 14e) (45 mg, 0.2 mmol) and pseudothiohydantoin (35 mg, 0.3 mmol) in acetic acid (1 mL) was added sodium acetate (66 mg, 0.8 mol). The mixture was heated to 110° C. for 4 h. After cooling to room temperature, the ice water was added. The solid was collected by filtration, washed with water and dried. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 0%-5% methanol in methylene chloride in 30 min) afforded 6-[2-amino-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-4-ethoxy-quinoline-3-carbonitrile (30 mg, 47%) as a light yellow solid: LC-MS m/e 445 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe solid was collected by filtration
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-95fb67b45b9a4bd98586059bc6fc1bb4
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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