1-(3-Aminopropyl)-4-methylpiperazine → N-(4'-([3-(4-methylpiperazin-1-yl)propylamino]carbonyl)-6-methyl-1,1'-biphenyl-3-yl)-3-furamide

HRID 970223노트

반응식

HRID 970223 반응식
[O:1]1[CH:5]=[CH:4][C:3]([C:6]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([CH3:24])=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([C:21](O)=[O:22])=[CH:17][CH:16]=3)[CH:14]=2)=[O:7])=[CH:2]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[NH2:47][CH2:48][CH2:49][CH2:50][N:51]1[CH2:56][CH2:55][N:54]([CH3:57])[CH2:53][CH2:52]1.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:57][N:54]1[CH2:55][CH2:56][N:51]([CH2:50][CH2:49][CH2:48][NH:47][C:21]([C:18]2[CH:17]=[CH:16][C:15]([C:13]3[C:12]([CH3:24])=[CH:11][CH:10]=[C:9]([NH:8][C:6]([C:3]4[CH:4]=[CH:5][O:1][CH:2]=4)=[O:7])[CH:14]=3)=[CH:20][CH:19]=2)=[O:22])[CH2:52][CH2:53]1

참가 물질

6

반응물 4

HCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 691521465'-(3-Furoylamino)-2'-methyl-1,1'-biphenyl-4-carboxylic acid

생성물 1

HCID 69151853N-(4'-([3-(4-methylpiperazin-1-yl)propylamino]carbonyl)-6-methyl-1,1'-biphenyl-3-yl)-3-furamide수율 17%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5′-(3-Furoylamino)-2′-methyl-1,1′-biphenyl-4-carboxylic acid (50 mg, 0.156 mmol), TBTU (60 mg, 0.186 mmol), 1-(3-aminopropyl)-4-methylpiperazine (25 mg, 0.156 mmol) and DIPEA (81 μl, 0.467 mmol) in DMF (1 ml) were stirred at room temperature for 2 h. The DMF was evaporated under vacuum and the residue dissolved in chloroform and filtered through an aminopropyl SPE (3 g). The filtrate was purified by flash chromatography on silica, eluting with DCM/ethanol/ammonia (110:8:1), which after evaporation of the solvents under vacuum gave N-(4′-{[3-(4-methylpiperazin-1-yl)propylamino]carbonyl)-6-methyl-1,1′-biphenyl-3-yl)-3-furamide (12 mg, 17%). NMR; δH [2H6]-DMSO 9.91,(1H, s), 8.55,(1H, t), 8.35,(1H, s), 7.90,(2H, d), 7.78,(1H, t), 7.66,(1H, dd), 7.59,(1H, d), 7.43,(2H, d), 7.27,(1H, d), 6.98,(1H, m), 3.29,(2H, m), 2.48-2.20,(10H, m), 2.19,(3H, s), 2.13,(3H, s), 1.68,(2H, m). LCMS: retention time 2.37 min, MH+461.

후처리

  1. customThe DMF was evaporated under vacuum
  2. dissolutionthe residue dissolved in chloroform
  3. filtrationfiltered through an aminopropyl SPE (3 g)
  4. customThe filtrate was purified by flash chromatography on silica
  5. washeluting with DCM/ethanol/ammonia (110:8:1), which
  6. customafter evaporation of the solvents under vacuum

출처 및 근거

ORD 기록
ord-89c3bf37406e4b30913afc663b07bc45
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07309800B2

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