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 1796193노트

반응식

HRID 1796193 반응식
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

참가 물질

7

반응물 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

생성물 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]methanesulfonamide수율 75%

시약·촉매·용매 3

HCID 962Water용매HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d0355f98da074c819958a8fc65b4141a
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030138B2

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