1-Methylpiperazine → N-{6-methyl-4'-[(4-methylpiperazin-1-yl)carbonyl]-1,1'-biphenyl-3-yl}2-pyrrolidin-1-ylisonicotinamide

HRID 970222Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 970222
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:21])[C:10]2[CH:15]=[CH:14][N:13]=[C:12]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:11]=2)=[CH:4][C:3]=1[C:22]1[CH:27]=[CH:26][C:25]([C:28]([OH:30])=O)=[CH:24][CH:23]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C1C=CC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH3:74][N:75]1[CH2:80][CH2:79][NH:78][CH2:77][CH2:76]1>CN(C=O)C>[CH3:1][C:2]1[C:3]([C:22]2[CH:27]=[CH:26][C:25]([C:28]([N:78]3[CH2:79][CH2:80][N:75]([CH3:74])[CH2:76][CH2:77]3)=[O:30])=[CH:24][CH:23]=2)=[CH:4][C:5]([NH:8][C:9](=[O:21])[C:10]2[CH:15]=[CH:14][N:13]=[C:12]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)[CH:11]=2)=[CH:6][CH:7]=1

Komponenten

7

Edukt 5

HCID 531671-MethylpiperazineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 113501482'-Methyl-5'-[(2-pyrrolidin-1-ylisonicotinoyl)amino]-1,1'-biphenyl-4-carboxylic acid

Produkt 1

HCID 69151845N-{6-methyl-4'-[(4-methylpiperazin-1-yl)carbonyl]-1,1'-biphenyl-3-yl}2-pyrrolidin-1-ylisonicotinamideAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2′-Methyl-5′-[(2-pyrrolidin-1-ylisonicotinoyl)amino]-1,1′-biphenyl-4-carboxylic acid (40 mg, 0.1 mmol), HATU (38 mg, 0.1 mmol), HOBT (13 mg, 0.1 mmol), DIPEA (52 μl), and 1-methylpiperazine (15 mg, 0.12 mmol) were mixed in DMF (1 ml) and stirred at room temperature for 18 h. The solvent was evaporated under vacuum and the residue partitioned between DCM (5 ml) and aqueous sodium carbonate (1M, 5 ml). The organic phase was applied to a silica gel flash column and eluted with DCM/ethanol/ammonia (100:8:1 then 40:8:1), which after evaporation of the solvents under vacuum gave N-{6-methyl-4′-[(4-methylpiperazin-1-yl)carbonyl]-1,1′-biphenyl-3-yl}-2-pyrrolidin-1-ylisonicotinamide (14 mg, 29%). NMR; δH [2H6]-DMSO 10.26,(1H, s), 8.19,(1H, d), 7.69-7.67,(2H, m), 7.47-7.41,(4H, m), 7.29,(1H, d), 6.96,(1H, d), 6.86,(1H, s), 3.59,(2H, b), 3.43,(4H, m), 2.33,(6H, b), 2.21,(3H, s), 2.21,(3H, s), 1.95,(4H, m). MS: MH+484.

Aufarbeitung

  1. customThe solvent was evaporated under vacuum
  2. customthe residue partitioned between DCM (5 ml) and aqueous sodium carbonate (1M, 5 ml)
  3. washeluted with DCM/ethanol/ammonia (100:8:1
  4. custom40:8:1), which after evaporation of the solvents under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ad914e45d2c1420b8796026c9bfd2080
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07309800B2

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