5-[4-Methylsulfanyl-3-(morpholine-4-sulfonyl)-benzoylamino]-2-(2-{[4-methylsulfanyl-3-(morpholine-4-sulfonyl)-benzoylamino]-phenyl}-vinyl)-benzenesulfonic Acid, 2,2-Dimethylpropyl Ester → 5-[4-Methylsulfanyl-3-(morpholine-4-sulfonyl)-benzoylamino]-2-(2-{[4-methylsulfanyl-3-(morpholine-4-sulfonyl)-benzoylamino]-phenyl}-vinyl)-benzenesulfonic Acid

HRID 277589

반응식

HRID 277589 반응식
[CH3:1][S:2][C:3]1[CH:54]=[CH:53][C:6]([C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([CH:25]=[CH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[NH:33][C:34](=[O:52])[C:35]3[CH:40]=[CH:39][C:38]([S:41][CH3:42])=[C:37]([S:43]([N:46]4[CH2:51][CH2:50][O:49][CH2:48][CH2:47]4)(=[O:45])=[O:44])[CH:36]=3)=[C:14]([S:16]([O:19]CC(C)(C)C)(=[O:18])=[O:17])[CH:15]=2)=[O:8])=[CH:5][C:4]=1[S:55]([N:58]1[CH2:63][CH2:62][O:61][CH2:60][CH2:59]1)(=[O:57])=[O:56]>CN(C)C=O.[Cl-].C[N+](C)(C)C>[CH3:1][S:2][C:3]1[CH:54]=[CH:53][C:6]([C:7]([NH:9][C:10]2[CH:11]=[CH:12][C:13]([CH:25]=[CH:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[NH:33][C:34](=[O:52])[C:35]3[CH:40]=[CH:39][C:38]([S:41][CH3:42])=[C:37]([S:43]([N:46]4[CH2:51][CH2:50][O:49][CH2:48][CH2:47]4)(=[O:45])=[O:44])[CH:36]=3)=[C:14]([S:16]([OH:19])(=[O:18])=[O:17])[CH:15]=2)=[O:8])=[CH:5][C:4]=1[S:55]([N:58]1[CH2:63][CH2:62][O:61][CH2:60][CH2:59]1)(=[O:57])=[O:56]

참가 물질

4

반응물 1

HCID 572684895-[4-Methylsulfanyl-3-(morpholine-4-sulfonyl)-benzoylamino]-2-(2-{[4-methylsulfanyl-3-(morpholine-4-sulfonyl)-benzoylamino]-phenyl}-vinyl)-benzenesulfonic Acid, 2,2-Dimethylpropyl Ester

생성물 1

HCID 538917875-[4-Methylsulfanyl-3-(morpholine-4-sulfonyl)-benzoylamino]-2-(2-{[4-methylsulfanyl-3-(morpholine-4-sulfonyl)-benzoylamino]-phenyl}-vinyl)-benzenesulfonic Acid수율 43.2%

시약·촉매·용매 2

HCID 6379Tetramethylammonium chloride촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a solution of 5-[4-methylsulfanyl-3-(morpholine-4-sulfonyl)-benzoylamino]-2-(2-{[4-methylsulfanyl-3-(morpholine-4-sulfonyl)-benzoylamino]-phenyl}-vinyl)-benzenesulfonic acid, 2,2-dimethylpropyl ester (Example 58, 0.30 g, 0.31 mimol) in 10 mL of anhydrous dimethylformamide was added tetramethylammonium chloride (0.069 g, 0.62 mmol) and the solution purged with nitrogen. The mixture was then heated to 100° C. and its progress followed by analytical reverse phase HPLC. After two days no starting material remained and the reaction was cooled to room temperature. After filtering to remove excess tetramethylammonium chloride the mixture was concentrated to dryness and the purified using reverse phase HPLC (70% THF/water) as the eluant. Freeze drying overnight afforded 120 mg of the title compound as a yellow solid.(43%): 1HNMR (DMSO-d6) δ10.59 (s, 1H), 10.54 (s, 1H), 8.41 (dd, J=7 Hz, 2 Hz, 2H), 8.27 (m, 2H), 8.19 (d, J=16 Hz, 1H), 8.13 (d, J=2 Hz, 1H), 7.99 (dd, J=9 Hz, 2 Hz, 1H), 7.82 (d, J=8.5 Hz, 2), 7.79 (d J=7 Hz, 1H), 7.65 (dd, J=9 Hz, 2 Hz, 2H), 7.51 (d, J=8.5 Hz, 2H), 7.08 (d, J=16 Hz, 1H), 3.61 (m, 8H), 3.15 (m, 8H), 2.60 (s, 6H); MS (ES-NEG): [M−H]− 887; Anal. Calc. for C38H40N4O11S5-2.2H2O: C, 49.14; H, 4.82; N, 6.03. Found: C, 49.17; H, 5.07; N, 5.04. Analytical reverse phase HPLC shows compound is >90% pure.

후처리

  1. customthe solution purged with nitrogen
  2. temperaturethe reaction was cooled to room temperature
  3. filtrationAfter filtering
  4. customto remove excess tetramethylammonium chloride the mixture
  5. concentrationwas concentrated to dryness
  6. customFreeze drying overnight

출처 및 근거

ORD 기록
ord-07b3a34f2ddf4af5a60fc5b966b21149
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06355633B1

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