Acetic Acid → HCID 68630757, compound

HRID 1931507Notes

Reaction equation

HRID 1931507 reaction equation
[C:1]([OH:4])(=O)[CH3:2].ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC.O[NH:28][C:29]([C:31]1[CH:32]=[C:33]2[C:38](=[CH:39][CH:40]=1)[N:37]=[C:36]([NH:41][C@H:42]1[C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH2:44][CH2:43]1)[CH:35]=[CH:34]2)=[NH:30]>C(#N)C>[C@H:42]1([NH:41][C:36]2[CH:35]=[CH:34][C:33]3[C:38](=[CH:39][CH:40]=[C:31]([C:29]4[N:28]=[C:1]([CH3:2])[O:4][N:30]=4)[CH:32]=3)[N:37]=2)[C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH2:44][CH2:43]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178513233HCID 178513233, compound

Product 1

HCID 68630757HCID 68630757, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of acetic acid (30 mg, 0.5 mmol) in acetonitrile (2.15 ml) was added at room temperature 1-hydroxy-benzotriazole (95 mg, 0.6 mmol) and N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimid-hydrochloride (110 mg, 0.57 mmol). The mixture was allowed to stir for 3 h at room temperature and N-hydroxy-2-((R)-indan-1-ylamino)-quinoline-6-carboxamidine (107 mg, 0.34 mmol) was added together with acetonitrile (2.15 ml). The mixture was allowed to stir for 2 h at room temperature, evaporated to dryness and diluted with acetic acid (3.5 ml). The reaction mixture was allowed to stir for 2 h at 100° C., evaporated, poured into saturated NaHCO3 solution (40 ml) and extracted with ethyl acetate (3×50 ml). The combined organic layers were washed with brine (2×50 ml), dried (MgSO4) and evaporated. The crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (ethyl acetate/heptane) to yield the title compound as light yellow oil (110 mg, 64%).

Workup

  1. stirringto stir for 2 h at room temperature
  2. customevaporated to dryness
  3. additiondiluted with acetic acid (3.5 ml)
  4. stirringto stir for 2 h at 100° C.
  5. customevaporated
  6. additionpoured into saturated NaHCO3 solution (40 ml)
  7. extractionextracted with ethyl acetate (3×50 ml)
  8. washThe combined organic layers were washed with brine (2×50 ml)
  9. dry with materialdried (MgSO4)
  10. customevaporated
  11. customThe crude product was purified by flash chromatography (ethyl acetate/heptane) on silica gel and crystallization (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-8cf315acbc9d4331913d0a6ff6580641
Source dataset
uspto-grants-2012_05
Patent number
US08188284B2

Reaction notes

Loading…