4-(Morpholin-4-yl)benzoic acid → 6-(4-Morpholinophenyl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole

HRID 15028

反応式

[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11](O)=O)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.[NH2:16][N:17]1[C:21]([C:22]2[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=2)=[N:20][N:19]=[C:18]1[SH:34]>O=P(Cl)(Cl)Cl>[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[CH:15]=[CH:14][C:10]([C:11]3[S:34][C:18]4=[N:19][N:20]=[C:21]([C:22]5[CH:27]=[C:26]([O:28][CH3:29])[C:25]([O:30][CH3:31])=[C:24]([O:32][CH3:33])[CH:23]=5)[N:17]4[N:16]=3)=[CH:9][CH:8]=2)[CH2:3][CH2:2]1

参加物

実験手順

A mixture of 4-morpholinobenzoic acid (86 mg, 0.42 mmol) and 4-amino-3-mercapto-5-(3,4,5-trimethoxyphenyl)-4H-1,2,4-triazole (102 mg, 0.36 mmol) was refluxed in POCl3 (5 mL) for 2 h. The reaction mixture was cooled to room temperature and excess POCl3 was removed under vacuum. The residue was dissolved in ethyl acetate and washed with saturated NaHCO3. The organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The crude product was purified by chromatography (80% ethyl acetate/hexane; 1 mL methanol/100 mL of solvent) to give the title compound as a yellow solid (40 mg, 0.088 mmol, 24%). 1H NMR (CDCl3): 7.78 (m, 2H), 7.73 (s, 2H), 6.98 (m, 2H), 4.00 (s, 6H), 3.94 (s, 3H), 3.89 (m, 4H), 3.41 (m, 4H).

後処理

customexcess POCl3 was removed under vacuum
dissolutionThe residue was dissolved in ethyl acetate
washwashed with saturated NaHCO3
dry with materialThe organic layer was dried over anhydrous Na2SO4
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by chromatography (80% ethyl acetate/hexane; 1 mL methanol/100 mL of solvent)

出典と根拠

ORDレコード: ord-1a99ddf1b32949a193135c68e1c70694
出典データセット: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07732468B2

反応式

参加物

反応物 2

生成物 1

試薬・触媒・溶媒 1

実験手順

後処理

出典と根拠

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