Triethylamine → N-[3-[3-(Benzoylamino)(imino)methylphenyl]-2-(E)-propenyl]-N-[3-carbamoyl-4-[1-(4,5-dihydro-3H-pyrrol-2-yl)piperidin-4-yloxy]phenyl]methanesulfonamide

HRID 1796193Notes

Reaction equation

HRID 1796193 reaction equation
Cl.Cl.C(C1C=C(/[CH:12]=[CH:13]/[CH2:14][N:15]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH:27]3[CH2:32][CH2:31][N:30]([C:33]4[CH2:37][CH2:36][CH2:35][N:34]=4)[CH2:29][CH2:28]3)=[C:22]([C:38](=[O:40])[NH2:39])[CH:21]=2)[S:16]([CH3:19])(=[O:18])=[O:17])C=CC=1)(=N)N.[C:41]([O:49]C1C=CC([N+]([O-])=O)=CC=1)(=O)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.C([N:61]([CH2:64][CH3:65])CC)C>ClCCl.C(#N)C.O>[C:41]([NH:15][C:20]1[C:65]([CH:64]=[NH:61])=[C:24](/[CH:12]=[CH:13]/[CH2:14][N:15]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH:27]3[CH2:32][CH2:31][N:30]([C:33]4[CH2:37][CH2:36][CH2:35][N:34]=4)[CH2:29][CH2:28]3)=[C:22]([C:38](=[O:40])[NH2:39])[CH:21]=2)[S:16]([CH3:19])(=[O:18])=[O:17])[CH:23]=[CH:22][CH:21]=1)(=[O:49])[C:42]1[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 70396Benzoic acid, 4-nitrophenyl esterHCID 22180975N-[3-(3-amidinophenyl)-2-(E)-propenyl]-N-[3-carbamoyl-4-[1-(4,5-dihydro-3H-pyrrol-2-yl)piperidin-4-yloxy]phenyl]methanesulfonamide dihydrochloride

Product 1

HCID 86593748N-[3-[3-(Benzoylamino)(imino)methylphenyl]-2-(E)-propenyl]-N-[3-carbamoyl-4-[1-(4,5-dihydro-3H-pyrrol-2-yl)piperidin-4-yloxy]phenyl]methanesulfonamideYield 75%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-[3-(3-amidinophenyl)-2-(E)-propenyl]-N-[3-carbamoyl-4-[1-(4,5-dihydro-3H-pyrrol-2-yl)piperidin-4-yloxy]phenyl]methanesulfonamide dihydrochloride (0.30 g) obtained in example 99(b) in a mixture of dichloromethane (4 ml) and acetonitrile (4 ml) were added successively 4-nitrophenyl benzoate (0.15 g) and triethylamine (0.28 ml) with stirring under ice-cooling, and the resulting mixture was stirred at room temperature overnight. After stirring, the reaction mixture was diluted with dichloromethane, and the organic layer was washed successively with a 0.5N aqueous sodium hydroxide solution and a saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of dichloromethane and methanol (50:0˜47:3). The purified solid obtained was dissolved in water and then lyophilized to afford the title compound (0.24 g, yield: 75%) as a pale yellow amorphous solid.

Workup

  1. temperaturecooling
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. stirringAfter stirring
  4. washthe organic layer was washed successively with a 0.5N aqueous sodium hydroxide solution
  5. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue obtained
  8. customwas purified by chromatography on a silica gel column
  9. customThe purified solid obtained

Sources & evidence

ORD record
ord-d0355f98da074c819958a8fc65b4141a
Source dataset
uspto-grants-2006_04
Patent number
US07030138B2

Reaction notes

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