7H-Pyrrolo[1,2-c]imidazol-7-one,5,6-dihydro-(9CI) synthesis

3synthesis methods

Product Name:7H-Pyrrolo[1,2-c]imidazol-7-one,5,6-dihydro-(9CI)
CAS Number:426219-43-4
Molecular formula:C6H6N2O
Molecular Weight:122.12

1-Propanone, 3-broMo-1-(1H-iMidazol-5-yl)-, hydrobroMide (1:1)

1346155-45-0
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7H-Pyrrolo[1,2-c]imidazol-7-one,5,6-dihydro-(9CI)

426219-43-4
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$65.00/10mg

Yield:426219-43-4 61%

Reaction Conditions:

with triethylamine in acetonitrile at 70; for 2.5 h;

Steps:

4.5. 5,6-Dihydro-7H-pyrrolo[1,2-c]imidazol-7-one (6)

A solution of Et₃N (15.3 mL, 110 mmol) in CH₃CN (25 mL) was added dropwise to a hot (70 °C) suspension of 5 (28.5 g, 100 mmol) in CH₃CN (1100 mL) and the mixture was stirred at 70 °C for 2 h. Triethylamine (25 mL, 179 mmol) was then added to the mixture, and the solution was stirred at 70 °C for a further 30 min. After cooling to room temperature, the insoluble material was filtered off and the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and the insoluble material was again filtered off. The filtrate was concentrated under reduced pressure and the resulting residue was separated by chromatography on silica gel (CH₂Cl₂/5% ammonia in MeOH = 10:1) to give 6 (6.67 g, 61%) as a colorless powder. ¹H NMR(CDCl₃) δ: 3.24 (2H, t, J = 6.5 Hz), 4.41 (2H, t, J = 6.5 Hz), 7.60 (1H, s), 7.74 (1H, s). IR(KBr): 3121, 1713, 1537, 1489, 1412, 1319, 1204, 1109 cm^-1.

References:

Ruchelman, Alexander L.;Man, Hon-Wah;Chen, Roger;Liu, Wei;Lu, Ling;Cedzik, Dorota;Zhang, Ling;Leisten, Jim;Collette, Alice;Narla, Rama Krishna;Raymon, Heather K.;Muller, George W. [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 21,p. 6356 - 6374] Location in patent:experimental part

3-BROMO-1-(1H-IMIDAZOL-5-YL)PROPAN-1-ONE

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426219-43-4
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References

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426219-43-4
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$65.00/10mg

References