1-(1-Ethylpiperazin-4-yl)-3-bromoisoquinoline → 1-(4-ethylpiperazin-1-yl)-3-[4-[N-(2-benzyloxyethyl)sulfamoyl]phenyl)isoquinoline

HRID 1251218ノート

反応式

HRID 1251218 の反応式
[CH2:1]([O:8][CH2:9][CH2:10][NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([Sn](CCCC)(CCCC)CCCC)=[CH:17][CH:16]=1)(=[O:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:35]1[N:36]=[C:37]([N:45]2[CH2:50][CH2:49][N:48]([CH2:51][CH3:52])[CH2:47][CH2:46]2)[C:38]2[C:43]([CH:44]=1)=[CH:42][CH:41]=[CH:40][CH:39]=2>C1(C)C(C)=CC=CC=1.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>[CH2:51]([N:48]1[CH2:47][CH2:46][N:45]([C:37]2[C:38]3[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH:44]=[C:35]([C:18]3[CH:17]=[CH:16][C:15]([S:12](=[O:13])(=[O:14])[NH:11][CH2:10][CH2:9][O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[CH:20][CH:19]=3)[N:36]=2)[CH2:50][CH2:49]1)[CH3:52]

参加物

5

反応物 2

HCID 225024471-(1-Ethylpiperazin-4-yl)-3-bromoisoquinolineHCID 69183332N-(2-Benzyloxyethyl)4-tributylstannylbenzenesulfonamide

生成物 1

HCID 225032411-(4-ethylpiperazin-1-yl)-3-[4-[N-(2-benzyloxyethyl)sulfamoyl]phenyl)isoquinoline収率 48.8%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 7237O-Xylene溶媒

実験手順

N-(2-Benzyloxyethyl)4-tributylstannylbenzenesulfonamide (0.92 g) and 3-bromo-1-(4-ethylpiperazin-1-yl)isoquinoline (0.42 g) were heated under reflux in the presence of tetrakistriphenylphosphinepalladium(0) (0.09 g) in xylene in nitrogen atmosphere for 45 min. After cooling, the reaction solution was filtered and concentrated. The residue was purified by silica gel column chromatography (chloroform/methanol system). The resulting product was dissolved in ethyl acetate and extracted with 2N hydrochloric acid. The aqueous layer was washed with ethyl acetate, adjusted to pH 10 with a 8N aqueous solution of sodium hydroxide, and then extracted with ethyl acetate. The extract was washed with a 10% aqueous solution of sodium carbonate and brine, and dried over magnesium sulfate. The solvent was evaporated, to give 1-(4-ethylpiperazin-1-yl)-3-{4-[N-(2-benzyloxyethyl)sulfamoyl]phenyl}isoquinoline (0.34 g) as a pale brown oil.

後処理

  1. temperatureAfter cooling
  2. filtrationthe reaction solution was filtered
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography (chloroform/methanol system)
  5. dissolutionThe resulting product was dissolved in ethyl acetate
  6. extractionextracted with 2N hydrochloric acid
  7. washThe aqueous layer was washed with ethyl acetate
  8. extractionextracted with ethyl acetate
  9. washThe extract was washed with a 10% aqueous solution of sodium carbonate and brine
  10. dry with materialdried over magnesium sulfate
  11. customThe solvent was evaporated

出典と根拠

ORDレコード
ord-7fe79025700a4412b68db2fd22ca347e
出典データセット
uspto-grants-2002_01
特許番号
US06340759B1

反応ノート

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