Acetic Acid → HCID 24986419, compound

HRID 1170201Notes

Reaction equation

HRID 1170201 reaction equation
[C:1](O)(=O)[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.[OH:17][NH:18][C:19]([C:21]1[C:22]2[CH:23]=[CH:24][C:25]([NH:31][CH2:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=3[O:39][CH3:40])=[N:26][C:27]=2[CH:28]=[CH:29][CH:30]=1)=[NH:20]>C1COCC1>[CH3:40][O:39][C:34]1[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=1[CH2:32][NH:31][C:25]1[CH:24]=[CH:23][C:22]2[C:27](=[CH:28][CH:29]=[CH:30][C:21]=2[C:19]2[N:20]=[C:1]([CH3:2])[O:17][N:18]=2)[N:26]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 682631,1'-CarbonyldiimidazoleHCID 178489480HCID 178489480, compound

Product 1

HCID 24986419HCID 24986419, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of acetic acid (48 mg, 0.8 mmol) in THF (7.5 ml) was added at room temperature 1,1′-carbonyl-diimidazole (151 mg, 0.93 mmol). The mixture was allowed to stir for 15 min at room temperature and for 90 min at 70° C., cooled to room temperature and N-hydroxy-2-(2-methoxy-benzylamino)-quinoline-5-carboxamidine (200 mg, 0.62 mmol) was added. The reaction mixture was allowed to stir at room temperature for 30 min, evaporated to dryness and diluted with acetic acid (7.5 ml). The reaction mixture was allowed to stir for 2 h at 100° C., evaporated, poured into saturated NaHCO3 solution (20 ml) and extracted with ethyl acetate (2×30 ml). The combined organic layers were washed with brine (20 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (dichloromethane/hexane) to yield the title compound as white solid (108 mg, 50%).

Workup

  1. temperaturecooled to room temperature
  2. stirringto stir at room temperature for 30 min
  3. customevaporated to dryness
  4. additiondiluted with acetic acid (7.5 ml)
  5. stirringto stir for 2 h at 100° C.
  6. customevaporated
  7. additionpoured into saturated NaHCO3 solution (20 ml)
  8. extractionextracted with ethyl acetate (2×30 ml)
  9. washThe combined organic layers were washed with brine (20 ml)
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. customThe crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (dichloromethane/hexane)

Sources & evidence

ORD record
ord-48ccd85cc25243fba5774cced4ddb010
Source dataset
uspto-grants-2010_11
Patent number
US07825253B2

Reaction notes

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