Triethylamine → 1-[1-(2-toluoylmethyl)-2-oxo-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-methoxycarbonyl-4-methylphenyl)urea

HRID 1979436ノート

反応式

HRID 1979436 の反応式
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Cl[C:14](Cl)([O:16]C(=O)OC(Cl)(Cl)Cl)Cl.C(N(CC)CC)C.[C:32]1([CH3:62])[C:33]([C:38]([CH2:40][N:41]2[C:47]3[CH:48]=[C:49]([CH3:52])[CH:50]=[CH:51][C:46]=3[N:45]([C:53](=[O:59])[C:54]3[S:58][CH:57]=[CH:56][CH:55]=3)[CH2:44][CH:43]([NH2:60])[C:42]2=[O:61])=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=1>O1CCCC1.O>[C:32]1([CH3:62])[C:33]([C:38]([CH2:40][N:41]2[C:47]3[CH:48]=[C:49]([CH3:52])[CH:50]=[CH:51][C:46]=3[N:45]([C:53](=[O:59])[C:54]3[S:58][CH:57]=[CH:56][CH:55]=3)[CH2:44][CH:43]([NH:60][C:14]([NH:12][C:9]3[CH:10]=[CH:11][C:2]([CH3:1])=[C:3]([C:4]([O:6][CH3:7])=[O:5])[CH:8]=3)=[O:16])[C:42]2=[O:61])=[O:39])=[CH:34][CH:35]=[CH:36][CH:37]=1

参加物

7

反応物 4

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 15049977Methyl 5-Amino-2-methylbenzoateHCID 212017831-(2-toluoylmethyl)-2-oxo-3-amino-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine

生成物 1

HCID 212020311-[1-(2-toluoylmethyl)-2-oxo-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepin-3-yl]-3-(3-methoxycarbonyl-4-methylphenyl)urea収率 252.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Methyl 2-methyl-5-aminobenzoate (0.37 g) was dissolved in tetrahydrofuran (10 ml), triphosgene (0.22 g) was added at internal temperature 5° C., triethylamine (0.95 g) was added thereto over 10 minutes, the mixture was stirred at room temperature for 10 minutes. A solution of 1-(2-toluoylmethyl)-2-oxo-3-amino-5-(2-thenoyl)-8-methyl-1,3,4,5-tetrahydro-2H-1,5-benzodiazepine (0.81 g) in tetrahydrofuran (10 ml) was added, the mixture was stirred at room temperature for one hour. Water was added to the reaction mixture, and extracted with chloroform. The organic layer was successively washed with water and saturated brine and dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography(chloroform:methanol=50:1), to thereby obtain 1.17 g of the title compound as light yellow amorphous (Yield: 100%).

後処理

  1. additionwas added
  2. stirringthe mixture was stirred at room temperature for one hour
  3. extractionextracted with chloroform
  4. washThe organic layer was successively washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography(chloroform:methanol=50:1)

出典と根拠

ORDレコード
ord-9d597a38403241748585ad8bf55d5730
出典データセット
uspto-grants-2001_05
特許番号
US06239131B1

反応ノート

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