2-(4-Oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid → 2-{5-[1-[5-(4-Morpholin-4-yl-phenyl)-furan-2-yl]-meth-(e)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid

HRID 2197687

反応式

HRID 2197687 の反応式
[O:1]=[C:2]1[CH2:6][S:5][C:4](=[S:7])[N:3]1[NH:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=[O:12].[N:18]1([C:24]2[CH:29]=[CH:28][C:27]([C:30]3[O:34][C:33]([CH:35]=O)=[CH:32][CH:31]=3)=[CH:26][CH:25]=2)[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1.C(O)(=O)C.C(O)(=O)C.C(N)CN.S([O-])(O)=O.[Na+]>CO>[N:18]1([C:24]2[CH:25]=[CH:26][C:27]([C:30]3[O:34][C:33](/[CH:35]=[C:6]4\[C:2](=[O:1])[N:3]([NH:8][C:9]5[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=5[C:11]([OH:13])=[O:12])[C:4](=[S:7])[S:5]\4)=[CH:32][CH:31]=3)=[CH:28][CH:29]=2)[CH2:19][CH2:20][O:21][CH2:22][CH2:23]1

参加物

6

反応物 4

HCID 45943372-(4-Oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acidHCID 10154317Ethylenediamine diacetateHCID 23665763Sodium BisulfiteHCID 594462295-(4-Morpholin-4-yl-phenyl)-furan-2-carbaldehyde

生成物 1

HCID 247757292-{5-[1-[5-(4-Morpholin-4-yl-phenyl)-furan-2-yl]-meth-(e)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid収率 87.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 2-(4-oxo-2-thioxo-thiazolidin-3-ylamino)-benzoic acid (0.089 g, 0.33 mmol), 5-(4-morpholin-4-yl-phenyl)-furan-2-carbaldehyde (0.091 g, 0.35 mmol) and ethylenediamine diacetate (0.063 g, 0.035 mmol) in methanol (10 mL) was stirred at room temperature for 18 h. The reaction mixture was poured into stirred 0.6 N aq sodium hydrogensulfite (50 mL). The mixture was vigorously stirred for 30 mm. The solid product was filtered off and washed on funnel successively with 0.6 N aq sodium hydrogensulfite (1 mL), water (2×2 mL), ether (2×1 mL) and hexanes (2 mL). The material was dried in a vacuum oven at 65° C. for 17 h to afford 2-{5-[1-[5-(4-morpholin-4-yl-phenyl)-furan-2-yl]-meth-(E)-ylidene]-4-oxo-2-thioxo-thiazolidin-3-ylamino}-benzoic acid (147 mg, 87%) as a solid. 1H NMR (400 MHz, DMSO-d6): 3.26 (2H, m), 3.76 (2H, m), 6.53 (1H, d, J=8.4 Hz), 6.87 (1H, m), 7.14 (2H, m), 7.17 (1H, d, J=3.6 Hz), 7.31 (1H, m), 7.40 (1H, d, J=4.0 Hz), 7.71 (1H, s), 7.76 (2H, m), 7.91 (1H, m), 10.4 (1H, bs). LC/MS: APCI 506.1, HPLC 92%.

後処理

  1. additionThe reaction mixture was poured
  2. stirringThe mixture was vigorously stirred for 30 mm
  3. filtrationThe solid product was filtered off
  4. washwashed on funnel successively with 0.6 N aq sodium hydrogensulfite (1 mL), water (2×2 mL), ether (2×1 mL) and hexanes (2 mL)
  5. customThe material was dried in a vacuum oven at 65° C. for 17 h

出典と根拠

ORDレコード
ord-0d282683e76540f7a65adc92a75b9e32
出典データセット
uspto-grants-2012_12
特許番号
US08338465B2

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