Hydrogen Peroxide → 2-(Ethylamino)-4-(5-(4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl)isoquinolin-1-yl)benzamide

HRID 1403076노트

반응식

HRID 1403076 반응식
Cl[C:2]1[C:11]2[C:6](=[C:7]([N:12]3[CH:16]=[C:15]([C:17]4[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=4)[N:14]=[CH:13]3)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.[C:23]([C:25]1[CH:30]=[CH:29][C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][C:26]=1[NH:40][CH2:41][CH3:42])#[N:24].C(=O)([O-])[O-:44].[Na+].[Na+].[OH-].[Na+].OO>COCCOC.CS(C)=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O.C(O)C>[CH2:41]([NH:40][C:26]1[CH:27]=[C:28]([C:2]2[C:11]3[C:6](=[C:7]([N:12]4[CH:16]=[C:15]([C:17]5[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=5)[N:14]=[CH:13]4)[CH:8]=[CH:9][CH:10]=3)[CH:5]=[CH:4][N:3]=2)[CH:29]=[CH:30][C:25]=1[C:23]([NH2:24])=[O:44])[CH3:42]

참가 물질

11

반응물 5

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 898866621-Chloro-5-(4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl)isoquinolineHCID 1300535754-Cyano-3-(ethylamino)phenylboronic acid pinacol ester

생성물 1

HCID 575206832-(Ethylamino)-4-(5-(4-(1-methyl-1H-pyrazol-4-yl)-1H-imidazol-1-yl)isoquinolin-1-yl)benzamide수율 45%

시약·촉매·용매 5

HCID 178418397HCID 178418397, 화합물촉매HCID 679Dimethyl Sulfoxide용매HCID 702Ethanol용매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

실험 절차

Pd(PPh3)4 (0.012 g) was added to a solution of compound (1d) (0.062 g), 4-cyano-3-(ethylamino)phenylboronic acid pinacol ester (0.071 g), and an aqueous sodium carbonate solution (2 M, 1.5 mL) in ethylene glycol dimethyl ether (3.0 mL) in a nitrogen atmosphere, and the mixture was stirred at 85° C. for 3 hours. The reaction solution was partitioned between ethyl acetate and water. The organic layer was washed with brine and then dried over anhydrous sodium sulfate. The solvent was distilled off, and the obtained residue was used in the next reaction. An aqueous sodium hydroxide solution (4 M, 0.093 mL) and a 30% aqueous hydrogen peroxide solution (0.045 mL) were added to a solution of the obtained residue in DMSO (3 mL) and ethanol (1.5 mL) at room temperature, and the mixture was stirred for 30 minutes. Water was added to the reaction solution, and the deposit was collected by filtration, then washed with water and ether by sprinkling, and then dried under reduced pressure to obtain compound (1) (0.040 g, yield based on 2 steps: 45%) as a pale yellow solid.

후처리

  1. customThe reaction solution was partitioned between ethyl acetate and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. customthe obtained residue was used in the next reaction
  6. filtrationthe deposit was collected by filtration
  7. washwashed with water and ether by sprinkling
  8. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-c6a3ffe0dba54245a36755dcd89f9bad
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912181B2

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