Tetrahydrofuran → HCID 57920003, compound

HRID 1882370Notes

Reaction equation

HRID 1882370 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([N:10]2[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=3[NH:12][C:11]2=[O:19])[S:5][C:6]=1[C:7]([O-:9])=[O:8].[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25]Br)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].O1CC[CH2:37][CH2:36]1>>[F:20][C:21]1[CH:28]=[CH:27][C:24]([CH2:25][N:12]2[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:10]([C:4]3[S:5][C:6]([C:7]([O:9][CH2:36][CH3:37])=[O:8])=[C:2]([CH3:1])[N:3]=3)[C:11]2=[O:19])=[CH:23][CH:22]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 11430Potassium Carbonate2×HCID 680214-Fluorobenzyl bromide3×HCID 86635200HCID 86635200, compound

Product 1

HCID 57920003HCID 57920003, compoundYield 59%

Procedure

To a 25-mL round bottom flask was added 4-methyl-2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)thiazole-5-carboxylate (0.10 g, 0.33 mmol), tetrahydrofuran (95 mL), 4-fluorobenzyl bromide (0.08 g, 0.43 mmol) and potassium carbonate (0.10 g, 0.73 mmol) at ambient temperature. The reaction mixture was stirred at ambient temperature for 16 h and refluxed for 3 h. The second portion of 4-fluorobenzyl bromide (0.08 g, 0.43 mmol) was added and stirred at ambient temperature for 17 h. The third portion of 4-fluorobenzyl bromide (0.08 g, 0.43 mmol) and second portion of potassium carbonate (0.10 g, 0.73 mmol) were added at ambient temperature. The mixture was stirred for an additional 3 h at ambient temperature, filtered and washed with tetrahydrofuran. The filtrate was concentrated and the residue was purified by column chromatography to afford the title compound as a white solid (0.08 g, 59% yield): mp 192-193° C.; 1H NMR (300 MHz, CDCl3) δ 8.58-8.55 (m, 1H), 7.38-7.31 (m, 2H), 7.26-7.16 (m, 2H), 7.05-6.95 (m, 3H), 5.09 (s, 2H), 4.32 (q, J=7.2 Hz, 2H), 2.76 (s, 3H), 1.36 (t, J=7.2 Hz, 3H); 13C NMR (75 MHz, CDCl3) δ 162.8, 157.1, 157.0, 151.9, 131.0, 131.0, 129.5, 129.4, 128.9, 126.3, 124.2, 122.9, 116.8, 116.1, 115.8, 115.0, 108.4, 61.0, 44.5, 17.5, 14.3; MS (ES+) m/z 412.0 (M+1).

Workup

  1. temperaturerefluxed for 3 h
  2. stirringstirred at ambient temperature for 17 h
  3. stirringThe mixture was stirred for an additional 3 h at ambient temperature
  4. filtrationfiltered
  5. washwashed with tetrahydrofuran
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-5123e87ea96a473085369a8e20fdb5e9
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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