Hydrochloric Acid → HCID 18542810, compound

HRID 1268158Notes

Reaction equation

HRID 1268158 reaction equation
[ClH:1].Cl.[C:3]([C:6]1[CH:7]=[CH:8][C:9]([F:34])=[C:10](/[CH:12]=[CH:13]/[CH2:14][N:15]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[CH:23][CH:22]=2)[S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])[CH:11]=1)(=[NH:5])[NH2:4].Cl.[C:36](=[NH:41])(OCC)[CH3:37].C(N(CC)CC)C.Cl>C(O)C.O1CCOCC1.CO>[ClH:1].[ClH:1].[C:36]([N:31]1[CH2:30][CH2:29][CH:28]([O:27][C:24]2[CH:25]=[CH:26][C:21]([N:15]([CH2:14]/[CH:13]=[CH:12]/[C:10]3[CH:11]=[C:6]([C:3](=[NH:4])[NH2:5])[CH:7]=[CH:8][C:9]=3[F:34])[S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])=[CH:22][CH:23]=2)[CH2:33][CH2:32]1)(=[NH:41])[CH3:37]

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8471TriethylamineHCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 18542630HCID 18542630, compound

Product 1

HCID 18542810HCID 18542810, compoundYield 144.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of N-[3-(5-amidino-2-fluorophenyl)-2-(E)-propenyl]-N-[4-(piperidin-4-yloxy)phenyl]ethanesulfonamide dihydrochloride (534 mg) in ethanol (20 ml) were added ethyl acetimidate hydrochloride (371 mg) and triethylamine (0.70 ml) at room temperature. The resulting mixture was stirred at room temperature for 12 hours. After addition of a 4M solution of hydrogen chloride in dioxane (2 ml), the resulting mixture was concentrated in vacuo. The residue was purified by preparative HPLC (YMC-Pack ODS YMC) using 20% aqueous acetonitrile as an eluant to afford an amorphous solid. To a solution of the solid in methanol (10 ml) was added a 4M solution of hydrogen chloride in dioxane (0.5 ml) and the mixture was concentrated to dryness in vacuo. The resulting amorphous solid was dissolved in water (10 ml) and the solution was lyophilized to give the title compound (415 mg, yield 75%) as a colorless amorphous solid.

Workup

  1. concentrationthe resulting mixture was concentrated in vacuo
  2. customThe residue was purified by preparative HPLC (YMC-Pack ODS YMC)
  3. customto afford an amorphous solid
  4. concentrationthe mixture was concentrated to dryness in vacuo
  5. dissolutionThe resulting amorphous solid was dissolved in water (10 ml)

Sources & evidence

ORD record
ord-951d77d33552467a909e884488784587
Source dataset
uspto-grants-2003_04
Patent number
US06555556B1

Reaction notes

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