Isopropylamine → 2-{[1-(3,5-dichloro-2-hydroxy-benzyl)-piperidin-4-ylmethyl]-amino}-1H-benzimidazole-4-carboxylic acid isopropylamide

HRID 2110007ノート

反応式

HRID 2110007 の反応式
[Cl:1][C:2]1[C:3]([OH:30])=[C:4]([CH:26]=[C:27]([Cl:29])[CH:28]=1)[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][NH:13][C:14]2[NH:18][C:17]3[CH:19]=[CH:20][CH:21]=[C:22]([C:23](O)=[O:24])[C:16]=3[N:15]=2)[CH2:8][CH2:7]1.O.O[N:33]1[C:37]2[CH:38]=CC=C[C:36]=2N=N1.C(N)(C)C.C(N=C=NC(C)C)(C)C>CN(C)C=O.CO>[CH:37]([NH:33][C:23]([C:22]1[C:16]2[N:15]=[C:14]([NH:13][CH2:12][CH:9]3[CH2:8][CH2:7][N:6]([CH2:5][C:4]4[CH:26]=[C:27]([Cl:29])[CH:28]=[C:2]([Cl:1])[C:3]=4[OH:30])[CH2:11][CH2:10]3)[NH:18][C:17]=2[CH:19]=[CH:20][CH:21]=1)=[O:24])([CH3:38])[CH3:36]

参加物

7

反応物 4

HCID 6363IsopropylamineHCID 12734DiisopropylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 690711862-{[1-(3,5-dichloro-2-hydroxy-benzyl)-piperidin-4-ylmethyl]-amino}-1H-benzimidazole-4-carboxylic acid

生成物 1

HCID 98917412-{[1-(3,5-dichloro-2-hydroxy-benzyl)-piperidin-4-ylmethyl]-amino}-1H-benzimidazole-4-carboxylic acid isopropylamide

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
40 °C

実験手順

2-{[1-(3,5-Dichloro-2-hydroxy-benzyl)-piperidin-4-ylmethyl]-amino}-1H-benzimidazole-4-carboxylic acid (30.0 mg, 0.0668 mmol) was suspended in dimethylformamide (0.50 ml). After adding 1-hydroxybenzotriazole monohydrate (30.6 mg, 0.200 mmol), isopropylamine (11.8 mg, 0.200 mmol) and diisopropylcarbodiimide (30.8 μl, 0.200 mmol) thereto, the mixture was stirred at 40° C. overnight. Methanol (2 ml) was added to the reaction mixture, and after stirring for 10 minutes, the reaction mixture was passed through SCX (Bond Elute SCX500MG) and the SCX was washed with methanol. After elution with a 2N ammonia-methanol solution, the solvent was distilled off under reduced pressure to obtain a residue. The residue was purified by preparative HPLC to obtain 2-{[1-(3,5-dichloro-2-hydroxy-benzyl)-piperidin-4-ylmethyl]-amino}-1H-benzimidazole-4-carboxylic acid isopropylamide. The compound was identified by LC-MS.

後処理

  1. stirringafter stirring for 10 minutes
  2. washthe reaction mixture was passed through SCX (Bond Elute SCX500MG)
  3. washthe SCX was washed with methanol
  4. washAfter elution with a 2N ammonia-methanol solution
  5. distillationthe solvent was distilled off under reduced pressure
  6. customto obtain a residue
  7. customThe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-8c69f0d09dc54ee5b37dd9fe985be6b3
出典データセット
uspto-grants-2009_04
特許番号
US07517875B2

反応ノート

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