Potassium Carbonate → HCID 59489553, compound

HRID 1879210Notes

Reaction equation

HRID 1879210 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][NH:7][C:8]([C:10]2[S:14][C:13]([C:15]3[NH:16][N:17]=[CH:18][CH:19]=3)=[N:12][C:11]=2[CH3:20])=[O:9])=[CH:4][CH:3]=1.Br[CH2:24][CH2:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.C(OCC)(=O)C>[F:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][NH:7][C:8]([C:10]2[S:14][C:13]([C:15]3[CH:19]=[CH:18][N:17]([CH2:24][CH2:25][O:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[N:16]=3)=[N:12][C:11]=2[CH3:20])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 68526Benzene, (2-bromoethoxy)-HCID 68489655HCID 68489655, compound

Product 1

HCID 59489553HCID 59489553, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A solution of 4-methyl-2-(2H-pyrazol-3-yl)-thiazole-5-carboxylic acid 4 fluoro-benzylamide (0.1 g, 0.33 mmol) in dimethyl sulfoxide (5 mL) was treated with (2-bromo-ethoxy)benzene (0.11 g, 0.50 mmol) and potassium carbonate (0.14 g, 1.0 mmol), and the reaction mixture was heated to 90° C. for 16 hr. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (50 mL), and washed with brine (2×50 mL). The organic phase was dried (Na2SO4) and evaporated. The residue was purified by preparative thin layer chromatography over silica gel (methylene chloride:methanol, 95:5) to provide 4-methyl-2-[1-(2-phenoxy-ethyl)-1H-pyrazol-3-yl]-thiazole-5-carboxylic acid 4-fluoro-benzylamide as a tan solid (0.061 g, 43% yield). 1H NMR (400 MHz, CDCl3) δ 7.46 (s, 1H), 7.07-7.19 (m, 5H), 6.78-6.93 (m, 3H), 6.70-6.73 (m, 2H), 5.82-5.88 (bm, 1H), 4.38-4.44 (m, 4H), 4.20 (t, J=5 Hz, 2H), 2.60 (s, 3H); MS (M+H)+=437.1; Rt=1.51 min; HRMS (M+H)+=437.14.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with brine (2×50 mL)
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by preparative thin layer chromatography over silica gel (methylene chloride:methanol, 95:5)

Sources & evidence

ORD record
ord-de29651985544d33bfe332905cb2c7de
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

Loading…