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

반응식

HRID 15028 반응식
[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

참가 물질

4

반응물 2

HCID 3452784-(Morpholin-4-yl)benzoic acidHCID 178488244HCID 178488244, 화합물

생성물 1

HCID 249552286-(4-Morpholinophenyl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole수율 24.4%

시약·촉매·용매 1

HCID 24813Phosphorus oxychloride용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-1a99ddf1b32949a193135c68e1c70694
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732468B2

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