HCID 57268489、化合物 → HCID 53891787、化合物

HRID 277589

反応式

HRID 277589 の反応式
[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]

参加物

4

反応物 1

HCID 57268489HCID 57268489、化合物

生成物 1

HCID 53891787HCID 53891787、化合物収率 43.2%

試薬・触媒・溶媒 2

HCID 6379Tetramethylammonium chloride触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-07b3a34f2ddf4af5a60fc5b966b21149
出典データセット
uspto-grants-2002_03
特許番号
US06355633B1

関連ノート

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