Diisopropylethylamine → 3-(4-Allyloxy-2-methoxy-phenyl)-5-(4-isobutyl-5-methyl-thiophen-2-yl)-[1,2,4]oxadiazole

HRID 1676146노트

반응식

HRID 1676146 반응식
[CH2:1]([C:5]1[CH:6]=[C:7]([C:11]([OH:13])=O)[S:8][C:9]=1[CH3:10])[CH:2]([CH3:4])[CH3:3].[CH2:14]([O:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]([NH:24]O)=[NH:23])=[C:20]([O:28][CH3:29])[CH:19]=1)[CH:15]=[CH2:16].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C.C(OCC)C>[CH2:14]([O:17][C:18]1[CH:27]=[CH:26][C:21]([C:22]2[N:23]=[C:11]([C:7]3[S:8][C:9]([CH3:10])=[C:5]([CH2:1][CH:2]([CH3:3])[CH3:4])[CH:6]=3)[O:13][N:24]=2)=[C:20]([O:28][CH3:29])[CH:19]=1)[CH:15]=[CH2:16]

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 594978744-Isobutyl-5-methylthiophene-2-carboxylic acidHCID 178458445HCID 178458445, 화합물

생성물 1

HCID 673521943-(4-Allyloxy-2-methoxy-phenyl)-5-(4-isobutyl-5-methyl-thiophen-2-yl)-[1,2,4]oxadiazole수율 62.1%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 4-isobutyl-5-methyl-thiophene-2-carboxylic acid (505 mg, 2.55 mmol), 4-allyloxy-N-hydroxy-2-methoxy-benzamidine (611 mg, 2.75 mmol) and DIPEA (377 mg, 2.92 mmol) in DMF (10 mL) is added TBTU (882 mg, 2.75 mmol). The mixture is stirred at rt for 15 h before it is diluted with diethyl ether (100 mL) and washed with 1 N aq. NaOH (2×30 mL), 1 M aq. KHSO4 (30 mL) and brine (30 mL). The organic extract is dried (Na2SO4), filtered and evaporated. The yellow oily residue is dissolved in dry toluene (10 mL) and heated at 150° C. for 20 min in a microwave oven. The mixture is poured into diethyl ether (100 mL) and washed with brine (75 mL). The organic extract is dried (Na2SO4), filtered and evaporated to give 3-(4-allyloxy-2-methoxy-phenyl)-5-(4-isobutyl-5-methyl-thiophen-2-yl)-[1,2,4]oxadiazole (609 mg) as a yellow solid; LC-MS: tR=1.19 min, [M+1]=385.23.

후처리

  1. washwashed with 1 N aq. NaOH (2×30 mL), 1 M aq. KHSO4 (30 mL) and brine (30 mL)
  2. extractionThe organic extract
  3. dry with materialis dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe yellow oily residue is dissolved in dry toluene (10 mL)
  7. temperatureheated at 150° C. for 20 min in a microwave oven
  8. additionThe mixture is poured into diethyl ether (100 mL)
  9. washwashed with brine (75 mL)
  10. extractionThe organic extract
  11. dry with materialis dried (Na2SO4)
  12. filtrationfiltered
  13. customevaporated

출처 및 근거

ORD 기록
ord-87d80f81f7d94fb2891dd7873bc31f98
출처 데이터셋
uspto-grants-2011_08
특허 번호
US08003800B2

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