Acetic Acid → HCID 67095880, compound

HRID 2076326Notes

Reaction equation

HRID 2076326 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[C:32]2[CH:33]=[CH:34][C:35]([NH:41][C@H:42]3[C:50]4[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=4)[CH2:44][CH2:43]3)=[N:36][C:37]=2[CH:38]=[CH:39][CH:40]=1)=[NH:30]>C(#N)C>[C@H:42]1([NH:41][C:35]2[CH:34]=[CH:33][C:32]3[C:37](=[CH:38][CH:39]=[CH:40][C:31]=3[C:29]3[N:28]=[C:1]([CH3:2])[O:4][N:30]=3)[N:36]=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 178513278HCID 178513278, compound

Product 1

HCID 67095880HCID 67095880, compoundYield 26.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a stirred solution of acetic acid (127 mg, 2.12 mmol) in acetonitrile (8.5 ml) was added at room temperature 1-hydroxy-benzotriazole (403 mg, 2.98 mmol) and N-(3-dimethylaminopropyl)-N′-ethyl-carbodiimid-hydrochloride (465 mg, 2.43 mmol). The mixture was allowed to stir for 3 h at room temperature and N-hydroxy-2-((R)-indan-1-ylamino)-quinoline-5-carboxamidine (450 mg, 1.41 mmol) was added together with acetonitrile (7.5 ml). The mixture was allowed to stir for 2 h at room temperature, evaporated to dryness and diluted with acetic acid (14 ml). The reaction mixture was allowed to stir for 2 h at 100° C., evaporated, poured into saturated NaHCO3 solution (50 ml) and extracted with ethyl acetate (3×80 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 solid (130 mg, 18%).

Workup

  1. stirringto stir for 2 h at room temperature
  2. customevaporated to dryness
  3. additiondiluted with acetic acid (14 ml)
  4. stirringto stir for 2 h at 100° C.
  5. customevaporated
  6. additionpoured into saturated NaHCO3 solution (50 ml)
  7. extractionextracted with ethyl acetate (3×80 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-e24e0704680f4ee5a91a798f981fde88
Source dataset
uspto-grants-2011_04
Patent number
US07923561B2

Reaction notes

Loading…