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Triethylamine → N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-3-methyl-2-thiophenecarboxamide

HRID 3490
ノート
印刷プレビュー

反応式

HRID 3490 の反応式
[CH3:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](Cl)=[O:8].C(N(CC)CC)C.[NH2:17][C:18]1[CH:39]=[CH:38][C:21]([C:22]([N:24]2[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=3[CH2:28][N:27]3[CH:35]=[CH:36][CH:37]=[C:26]3[CH2:25]2)=[O:23])=[CH:20][CH:19]=1>C(Cl)Cl>[CH:37]1[CH:36]=[CH:35][N:27]2[CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[N:24]([C:22]([C:21]3[CH:20]=[CH:19][C:18]([NH:17][C:7]([C:3]4[S:4][CH:5]=[CH:6][C:2]=4[CH3:1])=[O:8])=[CH:39][CH:38]=3)=[O:23])[CH2:25][C:26]=12
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 8471TriethylamineHCID 27376053-Methyl-2-thenoyl ChlorideHCID 1082828010,11-dihydro-10(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine

生成物 1

HCID 15340667N-[4-(5H-pyrrolo[2,1-c][1,4]benzodiazepin-10(11H)-ylcarbonyl)phenyl]-3-methyl-2-thiophenecarboxamide収率 113.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

実験手順

To a solution of 318 mg of 3-methyl-2-thiophenecarbonyl chloride in 5 ml of methylene chloride at 0° C. is added 346 μl of triethylamine. After stirring for 3 minutes, 500 mg of the 10,11-dihydro-10-(4-aminobenzoyl)-5H-pyrrolo[2,1-c][1,4]benzodiazepine is added. The bath is removed and the reaction mixture stirred at room temperature for 18 hours. The volatiles are concentrated in vacuo to give a residue which crystallizes from ethyl acetate to afford 800 mg of solid. The solid is dissolved in methylene chloride washed with water, 2N citric acid, 1M NaHCO3 and brine. The organic layer is filtered through hydrous magnesium silicate, dried with Na2SO4 and concentrated in vacuo to give a residue which crystallizes from ethyl acetate to afford 400 mg of the desired product as a white solid, m.p. 232°-235° C.

後処理

  1. customThe bath is removed
  2. stirringthe reaction mixture stirred at room temperature for 18 hours
  3. concentrationThe volatiles are concentrated in vacuo
  4. customto give a residue which
  5. customcrystallizes from ethyl acetate

出典と根拠

ORDレコード
ord-27e8f2b8906a42fb97a235b7a925cc8e
出典データセット
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05733905

反応ノート

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