Acetic Acid → HCID 11753221, compound

HRID 132096Notes

Reaction equation

HRID 132096 reaction equation
C(O[C:6](=[O:39])[NH:7][CH:8]([CH2:30][C:31]1[CH:36]=[C:35]([F:37])[CH:34]=[C:33]([F:38])[CH:32]=1)[CH:9]([OH:29])[CH2:10][NH:11][C:12]1([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Br:28])[CH:23]=2)[CH2:21][CH2:20][C:15]2([O:19][CH2:18][CH2:17][O:16]2)[CH2:14][CH2:13]1)(C)(C)C.[CH3:40]N1CCOCC1.C(O)(=O)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>FC(F)(F)C(O)=O.C(Cl)Cl>[Br:28][C:24]1[CH:23]=[C:22]([C:12]2([NH:11][CH2:10][CH:9]([OH:29])[CH:8]([NH:7][C:6](=[O:39])[CH3:40])[CH2:30][C:31]3[CH:36]=[C:35]([F:37])[CH:34]=[C:33]([F:38])[CH:32]=3)[CH2:13][CH2:14][C:15]3([O:19][CH2:18][CH2:17][O:16]3)[CH2:20][CH2:21]2)[CH:27]=[CH:26][CH:25]=1

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 79724-MethylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 69548446HCID 69548446, compound

Product 1

HCID 11753221HCID 11753221, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

Compound 17 was dissolved in 1 mL (1:1) trifluoroacetic acid (TFA) and CH2Cl2. The reaction stirred at room temperature for 2 h and concentrated under reduced pressure. The residue was dissolved in 4 mL CH2Cl2 and N-Methylmorpholine (NMM) (3.12 mmol). The reaction was stirred at 0° C. Acetic Acid (0.76 mmol) was added slowly to the reaction mixture and the mixture stirred at 0° C. for five min. Then 1-Hydroxylbenzotriazole hydrate (HOBt) (0.76 mmol) and 1-Ethyl-3-(3′-Dimethylaminopropyl)carbodiimide Hydrochloride (EDC.HCl) (0.76 mmol) were added sequentially. The reaction was stirred at room temperature for two h. CH2Cl2 was removed by reduced pressure and the residue dissolved in EtOAc. The organic layer was rinsed with a saturated NaHCO3 solution three times and once with Brine. The organic layer was dried with MgSO4, filtered and concentrated under reduced pressure. Compound 22 was purified by preparative HPLC.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in 4 mL CH2Cl2
  3. stirringThe reaction was stirred at 0° C
  4. stirringthe mixture stirred at 0° C. for five min
  5. stirringThe reaction was stirred at room temperature for two h
  6. customCH2Cl2 was removed by reduced pressure
  7. dissolutionthe residue dissolved in EtOAc
  8. washThe organic layer was rinsed with a saturated NaHCO3 solution three times and once with Brine
  9. dry with materialThe organic layer was dried with MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customCompound 22 was purified by preparative HPLC

Sources & evidence

ORD record
ord-c580cf5b8e1f46e58de53e85d64d3e81
Source dataset
uspto-grants-2008_06
Patent number
US07385085B2

Reaction notes

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