Ethyl Acetate → HCID 178433998, compound

HRID 1882450Notes

Reaction equation

HRID 1882450 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][N:10]([C:13]2[S:14][C:15]([C:19]([NH2:21])=O)=[C:16]([CH3:18])[N:17]=2)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO[C:25](OC)([N:27](C)C)[CH3:26].O.[NH2:33]N.C(OCC)(=O)C>O1CCOCC1>[CH2:1]([N:8]1[CH2:12][CH2:11][N:10]([C:13]2[S:14][C:15]([C:19]3[NH:27][C:25]([CH3:26])=[N:33][N:21]=3)=[C:16]([CH3:18])[N:17]=2)[C:9]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 878351,1-Dimethoxyethyl(dimethyl)amineHCID 57919990HCID 57919990, compound

Product 1

HCID 178433998HCID 178433998, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(3-benzyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxamide (0.20 g, 0.63 mmol) in 1,4 dioxane (10 mL) was added N,N-dimethylacetamide dimethyl acetal (1.0 mL, 6.80 mmol). The reaction mixture was heated to reflux for 5 hours and concentrated in vacuo. The residue was dissolved in acetic acid (10 mL) and hydrazine monohydrate (0.1 mL, 2.0 mmol) was added. The reaction mixture was heated for 3 hours at 90° C. and concentrated in vacuo. The residue was dissolved in saturated sodium bicarbonate (10 mL) and extracted with chloroform. The organic solution was washed with water and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was triturated with ethyl acetate to afford the title in 65% yield (0.15 g): mp 284-287° C. (ethyl acetate); 1H NMR (300 MHz, DMSO-d6) δ 13.6 (br s, 1H), 7.33-7.26 (m, 5H), 4.40 (s, 2H), 3.99-3.94 (m, 2H), 3.44-3.39 (m, 2H), 2.52 (s, 3H), 2.33 (s, 3H); 13C NMR (75 MHz, DMSO-d6) δ 156.9, 155.7, 153.6, 145.6, 136.9, 129.1, 128.2, 127.9, 47.4, 42.4, 42.1, 17.1, 12.1; MS (ES+) m/z 355.2 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 hours
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in acetic acid (10 mL)
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in saturated sodium bicarbonate (10 mL)
  7. extractionextracted with chloroform
  8. washThe organic solution was washed with water and brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. concentrationThe filtrate was concentrated in vacuo
  12. customthe residue was triturated with ethyl acetate
  13. customto afford the title in 65% yield (0.15 g)

Sources & evidence

ORD record
ord-2c40727f9dae4450b3e887d2cc10912f
Source dataset
uspto-grants-2012_11
Patent number
US08318949B2

Reaction notes

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