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

HRID 323169

反応式

HRID 323169 の反応式
[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

参加物

7

反応物 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

生成物 1

HCID 220105624-(4'-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-[3-(4-methylpiperazin-1-ylcarbonyl)aminoprop-1-yl]phenyl]benzamide収率 29.8%

試薬・触媒・溶媒 3

HCID 11791229Dichloronickel;hexahydrate触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e9f4748e503148fcb5e4ea2d6bc5ad00
出典データセット
uspto-grants-2001_04
特許番号
US06211242B1

関連ノート

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