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

HRID 323169
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HRID 323169 반응식
[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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 11791229
Dichloronickel;hexahydrate
촉매
HCID 887Methanol용매
HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e9f4748e503148fcb5e4ea2d6bc5ad00
출처 데이터셋
uspto-grants-2001_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06211242B1

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