Triethylamine → N-[4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenyl]-4-methylphenylsulphonamide

HRID 1291809ノート

反応式

HRID 1291809 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]2)=[CH:3][CH:2]=1.Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][S:24]([C:27]2[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])=[CH:19][CH:18]=1)=[O:16].C(N(CC)CC)C>C(O)(C)C>[N:1]1[CH:6]=[CH:5][C:4]([N:7]2[CH2:8][CH2:9][N:10]([CH2:14][C:15]([C:17]3[CH:18]=[CH:19][C:20]([NH:23][S:24]([C:27]4[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][CH:28]=4)(=[O:25])=[O:26])=[CH:21][CH:22]=3)=[O:16])[CH2:11][CH2:12]2)=[CH:3][CH:2]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 705171-(4-Pyridyl)piperazineHCID 16637184N-[4-(2-Bromoacetyl)phenyl]-4-methylbenzenesulfonamide

生成物 1

HCID 18918408N-[4-[2-[4-(4-pyridyl)piperazin-1-yl]acetyl]phenyl]-4-methylphenylsulphonamide

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

A mixture of 1-(4-pyridyl)piperazine (1.79 g), N-(4-bromoacetylphenyl)-4-methylphenylsulphonamide (3.68 g) and triethylamine (1.39 ml) in isopropanol (50 ml) was stirred for 18 hours. The precipitated solid was collected, triturated with dichloromethane, filtered and dried. This solid was further purified by flash chromatography on neutral alumina eluting successively with dichloromethane, 2.5% v/v methanol/dichloromethane then 5% v/v methanol/dichloromethane. Evaporation of the desired fractions to a small volume followed by addition of dichloromethane gave a crystalline solid. This solid was collected, washed with dichloromethane to give the title compound, 440 mg, as crystals: m.p. 168°-170° C.; NMR (d6DMSO) δ 8.14(2H,d), 7.86(2H,d), 7.71(2H,d), 7.35(2H,d), 7.18(2H,d), 6.80(2H,d), 3.79(2H,s), 3.31(4H,t), 2.59(4H,t), 2.33(3H,s); m/e 451 (M+H)+ ; calculated for C24H26N4O3S: C, 64.0; H, 5.8; N, 12.4. found C, 63.4; H, 5.7; N, 12.2%.

後処理

  1. customThe precipitated solid was collected
  2. customtriturated with dichloromethane
  3. filtrationfiltered
  4. customdried
  5. customThis solid was further purified by flash chromatography on neutral alumina eluting successively with dichloromethane, 2.5% v/v methanol/dichloromethane
  6. customEvaporation of the desired fractions to a small volume
  7. additionfollowed by addition of dichloromethane
  8. customgave a crystalline solid
  9. customThis solid was collected
  10. washwashed with dichloromethane

出典と根拠

ORDレコード
ord-d3d90508e4d049fdaf7ca053fdff17f6
出典データセット
uspto-grants-1998_05
特許番号
US05753659

反応ノート

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