Diisopropylethylamine → HCID 178466950, compound

HRID 1297634Notes

Reaction equation

HRID 1297634 reaction equation
[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11](/[CH:14]=[C:15]3/[C:16](=[O:22])[N:17]=[C:18](SC)[S:19]/3)[CH:12]=2)[N:7]=[CH:6][C:5]=1[C:23]#[N:24])[CH3:2].[F:25][C:26]1[CH:27]=[C:28]([CH2:32][CH2:33][NH2:34])[CH:29]=[CH:30][CH:31]=1.C(N(C(C)C)CC)(C)C>C(#N)C>[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11](/[CH:14]=[C:15]3/[C:16](=[O:22])[N:17]=[C:18]([NH:34][CH2:33][CH2:32][C:28]4[CH:29]=[CH:30][CH:31]=[C:26]([F:25])[CH:27]=4)[S:19]/3)[CH:12]=2)[N:7]=[CH:6][C:5]=1[C:23]#[N:24])[CH3:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5339282-(3-Fluorophenyl)ethanamineHCID 585858204-Ethoxy-6-[2-methylsulfanyl-4-oxo-4h-thiazol-(5z)-ylidenemethyl]-quinoline-3-carbonitrile

Product 1

HCID 178466950HCID 178466950, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

The suspension of 4-ethoxy-6-[2-methylsulfanyl-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-quinoline-3-carbonitrile (example 14 g) (71 mg, 0.2 mmol), m-fluorophenylethylamine (28 ul, 0.22 mmol) and DIEA (diisopropylethylamine) (0.11 mL, 0.44 mmol) in acetonitrile (2 mL) was stirred under at 80° C. for 4 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%-5% methanol in methylene chloride in 30 min) afforded 4-ethoxy-6-[2-[2-(3-fluoro-phenyl)-ethylamino]-4-oxo-4H-thiazol-(5Z)-ylidenemethyl]-quinoline-3-carbonitrile (60 mg, 67%) as a light yellow solid: LC-MS m/e 447 (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-85505b1c49de4b9a834808afc5610f13
Source dataset
uspto-grants-2007_07
Patent number
US07250515B2

Reaction notes

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