(2-Thienylmethyl)amine → HCID 178518102, compound

HRID 2053295Notes

Reaction equation

HRID 2053295 reaction equation
CS[C:3]1[S:4]/[C:5](=[CH:9]\[C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)/[C:6](=[O:8])[N:7]=1.[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH2:25][NH2:26].C(N(C(C)C)CC)(C)C>C(#N)C>[S:20]1[CH:24]=[CH:23][CH:22]=[C:21]1[CH2:25][NH:26][C:3]1[S:4]/[C:5](=[CH:9]\[C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)/[C:6](=[O:8])[N:7]=1

Participants

5

Reactant 3

HCID 34005(2-Thienylmethyl)amineHCID 81531DiisopropylethylamineHCID 58585737(5Z)-2-(methylthio)-5-(6-quinolinylmethylidene)-1,3-thiazol-4(5H)-one

Product 1

HCID 178518102HCID 178518102, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

The suspension of 2-methylsulfanyl-5-[1-quinolin-6-yl-meth-(Z)-ylidene]-thiazol-4-one (example 1a, 3.0 g, 10.5 mmol), thiophene methyl amine (2.4 g, 21.0 mmol) and diisopropylethylamine (DIEA) (3.66 mL, 21.0 mmol) in acetonitrile (30 mL) was stirred under at 80° C. for 12 h. After cooling to room temperature, the solid was collected by filtration, washed with a little bit of acetonitrile and dried. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 0%-10% methanol in methylene chloride in 30 min) afforded 2-[(thiophen-2-ylmethyl)-amino]-5-[1-quinolin-6-yl-meth-(Z)-ylidene]-thiazol-4-one (2.5 g, 67%) as a light yellow solid: LC-MS m/e 352 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe solid was collected by filtration
  3. washwashed with a little bit of acetonitrile
  4. customdried

Sources & evidence

ORD record
ord-fecf5010f0904086aa3ed390d04bb641
Source dataset
uspto-grants-2008_02
Patent number
US07326786B2

Reaction notes

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