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

HRID 970223ノート

反応式

HRID 970223 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-89c3bf37406e4b30913afc663b07bc45
出典データセット
uspto-grants-2007_12
特許番号
US07309800B2

反応ノート

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