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Diisopropylethylamine → 1H-pyrrole-2-carboxylic acid [2-(5-benzenesulfonyl-1H-indazol-3-ylcarbamoyl)-5-(4-methyl-piperazin-1-yl)-phenyl]amide

HRID 1640982
ノート
印刷プレビュー

反応式

HRID 1640982 の反応式
[NH2:1][C:2]1[CH:28]=[C:27]([N:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)[CH:26]=[CH:25][C:3]=1[C:4]([NH:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[CH:14]=2)[NH:9][N:8]=1)=[O:5].C(N(CC)C(C)C)(C)C.[NH:45]1[CH:49]=[CH:48][CH:47]=[C:46]1[C:50](Cl)=[O:51]>ClCCl>[C:19]1([S:16]([C:13]2[CH:14]=[C:15]3[C:10](=[CH:11][CH:12]=2)[NH:9][N:8]=[C:7]3[NH:6][C:4]([C:3]2[CH:25]=[CH:26][C:27]([N:29]3[CH2:30][CH2:31][N:32]([CH3:35])[CH2:33][CH2:34]3)=[CH:28][C:2]=2[NH:1][C:50]([C:46]2[NH:45][CH:49]=[CH:48][CH:47]=2)=[O:51])=[O:5])(=[O:18])=[O:17])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 81531Diisopropylethylamine2 回HCID 224558Pyrrole-2-carbonyl chlorideHCID 594370872-amino-N-(5-benzenesulfonyl-1H-indazol-3-yl)-4-(4-methyl-piperazin-1-yl)-benzamide

生成物 1

HCID 248257521H-pyrrole-2-carboxylic acid [2-(5-benzenesulfonyl-1H-indazol-3-ylcarbamoyl)-5-(4-methyl-piperazin-1-yl)-phenyl]amide収率 20.6%

試薬・触媒・溶媒 1

HCID 6344
Dichloromethane
溶媒

実験手順

2-Amino-N-(5-benzenesulfonyl-1H-indazol-3-yl)-4-(4-methyl-piperazin-1-yl)-benzamide (245 mg, 0.5 mmol) was suspended in dichloromethane (10 mL), treated first with neat N,N-diisopropylethylamine (0.35 mL, 2 mmol) then with solid 1H-pyrrole-2-carbonyl chloride (258 mg, 2 mmol). The reaction was stirred at room temperature overnight then treated with additional acid chloride (258 mg) and N,N-diisopropylethylamine (0.35 mL). After two hours the solvent was removed under reduced pressure and the crude was taken up with tetrahydrofuran (30 mL) and treated with 2N NaOH (10 mL). After stirring overnight the solvent was removed and the solid was filtered and washed thoroughly with water. The crude was purified by flash chromatography over silica gel (eluent: ethyl acetate/methanol/aq.33% NH4OH in 9:1:0.1 ratio) to give 60 mg of title compound.

後処理

  1. customAfter two hours the solvent was removed under reduced pressure
  2. additiontreated with 2N NaOH (10 mL)
  3. stirringAfter stirring overnight the solvent
  4. customwas removed
  5. filtrationthe solid was filtered
  6. washwashed thoroughly with water
  7. customThe crude was purified by flash chromatography over silica gel (eluent: ethyl acetate/methanol/aq.33% NH4OH in 9:1:0.1 ratio)

出典と根拠

ORDレコード
ord-6ebd8670118846b6817fff1bb6421346
出典データセット
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08114865B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート