Diethyl Ether → 4-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-[3-(4-methylpiperazin-1-ylcarbonyl)aminoprop-1-yl]phenyl]benzamide

HRID 323169

Reaktionsgleichung

Reaktionsgleichung von HRID 323169
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:45]=[CH:44][C:20]([C:21]([N:23]([CH3:43])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[C:30]#[C:31][CH2:32][NH:33][C:34]([N:36]4[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]4)=[O:35])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[BH4-].[Na+].C(OCC)C>O1CCCC1.CO.O.O.O.O.O.O.[Ni](Cl)Cl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:45]=[CH:44][C:20]([C:21]([N:23]([CH3:43])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=4[CH2:30][CH2:31][CH2:32][NH:33][C:34]([N:36]4[CH2:37][CH2:38][N:39]([CH3:42])[CH2:40][CH2:41]4)=[O:35])=[O:22])=[CH:19][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 3283Diethyl EtherHCID 4311764Sodium borohydrideHCID 700701824-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-[3-(4-methylpiperazin-1-yl)carbonylamino-(1-propyn-1-yl)]phenyl]benzamide

Produkt 1

HCID 220105624-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-[3-(4-methylpiperazin-1-ylcarbonyl)aminoprop-1-yl]phenyl]benzamideAusbeute 29,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11791229Dichloronickel;hexahydrateKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To an ice cooled mixture of 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-[3-(4-methylpiperazin-1-yl)carbonylamino-(1-propyn-1-yl)]phenyl]benzamide (250 mg) and nickel chloride hexahydrate (297 mg) in a mixture of tetrahydrofuran (5 ml) and methanol (5 ml) was added sodium borohydride in small portions and the mixture was stirred at the same temperature for 1 hour. The mixture was filtered through bed of Celite and the filtrate was evaporated in vacuo. The residue was dissolved in chloroform (20 ml) and washed with water and brine. The organic solution was dried over magnesium sulfate and the solvent was evaporated in vacuo to give a syrup. The residue was solidified with diethyl ether to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-[3-(4-methylpiperazin-1-ylcarbonyl)aminoprop-1-yl]phenyl]benzamide (75.0 mg) as a powder.

Aufarbeitung

  1. filtrationThe mixture was filtered through bed of Celite
  2. customthe filtrate was evaporated in vacuo
  3. dissolutionThe residue was dissolved in chloroform (20 ml)
  4. washwashed with water and brine
  5. dry with materialThe organic solution was dried over magnesium sulfate
  6. customthe solvent was evaporated in vacuo
  7. customto give a syrup

Quellen und Nachweise

ORD-Eintrag
ord-e9f4748e503148fcb5e4ea2d6bc5ad00
Quelldatensatz
uspto-grants-2001_04
Patentnummer
US06211242B1

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