Diisopropylethylamine → 1-(2-Thiophen-2-yl-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl)-ethanone

HRID 2223490Notes

Reaction equation

HRID 2223490 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[S:8])[NH2:7].C(N(C(C)C)C(C)C)C.Br.[C:19]([N:22]1[CH2:27][CH2:26][C:25](=O)[CH:24](Br)[CH2:23]1)(=[O:21])[CH3:20]>C(#N)C>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[S:8][C:24]2[CH2:23][N:22]([C:19](=[O:21])[CH3:20])[CH2:27][CH2:26][C:25]=2[N:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 7372372-ThiophenecarbothioamideHCID 197611761-Acetyl-3-bromopiperidin-4-one hydrobromide

Product 1

HCID 685332071-(2-Thiophen-2-yl-6,7-dihydro-4H-thiazolo[5,4-c]pyridin-5-yl)-ethanone

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

2.8 mmol of thiophene-2-thiocarboxamide was dissolved in 10 ml acetonitrile. 5.6 mmol of N-ethyl-diisopropylamine was added, followed by 3.4 mmol 1-acetyl-3-bromo-piperidin-4-one hydrobromide (prepared according to patent U.S. Pat No. 4,122,083). The reaction mixture was heated to 50° C. for 4 hours, cooled and concentrated. Chromatography of the residue (SiO2; ethyl acetate) yields the title compound as a yellowish gum. MS (m/e): 265.0 (M+H+).

Workup

  1. temperaturecooled
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-36d31c6ba1bd421e8061582183de1a09
Source dataset
uspto-grants-2008_05
Patent number
US07375226B2

Reaction notes

Loading…