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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
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HRID 1640982 반응식
[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
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참가 물질

5

반응물 3

HCID 81531Diisopropylethylamine2회HCID 224558Pyrrole-2-carbonyl chlorideHCID 594370872-amino-N-(5-benzenesulfonyl-1H-indazol-3-yl)-4-(4-methyl-piperazin-1-yl)-benzamide

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-6ebd8670118846b6817fff1bb6421346
출처 데이터셋
uspto-grants-2012_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08114865B2

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