Diisopropylethylamine → HCID 178466912, compound

HRID 853020Notes

Reaction equation

HRID 853020 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[S:19][C:18](SC)=[N:17][C:16]3=[O:22])[CH:12]=2)[N:7]=[CH:6][CH:5]=1)[CH3:2].[F:23][C:24]1[CH:25]=[C:26]([CH2:30][CH2:31][NH2:32])[CH:27]=[CH:28][CH:29]=1.CCN(C(C)C)C(C)C>>[CH2:1]([O:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH:14]=[C:15]3[S:19][C:18]([NH:32][CH2:31][CH2:30][C:26]4[CH:27]=[CH:28][CH:29]=[C:24]([F:23])[CH:25]=4)=[N:17][C:16]3=[O:22])[CH:12]=2)[N:7]=[CH:6][CH:5]=1)[CH3:2]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 5339282-(3-Fluorophenyl)ethanamineHCID 694667775-(4-Ethoxy-quinolin-6-ylmethylene)-2-methylsulfanyl-thiazol-4-one

Product 1

HCID 178466912HCID 178466912, compoundYield 71.2%

Conditions

Temperature
80 °C

Procedure

The suspension of 5-(4-ethoxy-quinolin-6-ylmethylene)-2-methylsulfanyl-thiazol-4-one (example 40b) (100 mg, 0.3 mmol), m-fluorophenylethylamine (80 ul, 0.6 mmol) and DIEA (0.10 mL, 0.6 mmol) in acetoniltile (2 mL) was stirred under at 80° C. for 3 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 5-(4-ethoxy-quinolin-6-ylmethylene)-2-[2-(3-fluoro-phenyl)-ethylamino]-thiazol-4-one (90 mg, 70%) as a light yellow solid: LC-MS m/e 422 (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-99cb29f8a0324cdea6046f8a37c6969d
Source dataset
uspto-grants-2007_08
Patent number
US07253285B2

Reaction notes

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