Methanol → (1H-benzimidazol-2-yl)-[1-(1-methyl-1H-indol-2-ylmethyl)-piperidin-4-ylmethyl]-amine

HRID 2109989

반응식

HRID 2109989 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]1[CH:11]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[NH:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[NH:36][CH2:37][CH:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1.CO>CN(C)C=O.C(O)(=O)C>[NH:27]1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2[N:29]=[C:28]1[NH:36][CH2:37][CH:38]1[CH2:43][CH2:42][N:41]([CH2:11][C:3]2[N:2]([CH3:1])[C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH2:40][CH2:39]1

참가 물질

6

반응물 4

HCID 887MethanolHCID 2671641-Methylindole-2-carboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 11481631HCID 11481631, 화합물

생성물 1

HCID 10150398(1H-benzimidazol-2-yl)-[1-(1-methyl-1H-indol-2-ylmethyl)-piperidin-4-ylmethyl]-amine

시약·촉매·용매 1

HCID 21926011acetic acid N,N-dimethylformamide용매

실험 절차

After adding 1-methyl-1H-indole-2-carboaldehyde (0.26 mmol) and sodium triacetoxyborohydride (0.26 mmol) to a solution of (1H-benzimidazol-2-yl)-piperidin-4-ylmethyl-amine (20.0 mg, 0.09 mmol) in dimethylformamide-acetic acid (10:1) (1.0 ml), the mixture was stirred at room temperature overnight. Methanol (1.0 ml) was added to the reaction mixture to suspend the reaction, and after stirring for 1 hour, the solution was passed through SCX (Bond Elute SCX500MG: cationic ion-exchange resin, Varian). The SCX was washed with methanol and then with a mixed solution of chloroform/methanol (1/1), and elution was performed with a 2N ammonia-methanol solution. The solvent was distilled off under reduced pressure to obtain (1H-benzimidazol-2-yl)-[1-(1-methyl-1H-indol-2-ylmethyl)-piperidin-4-ylmethyl]-amine. The compound was identified by LC-MS.

후처리

  1. customthe reaction
  2. stirringafter stirring for 1 hour
  3. washthe solution was passed through SCX (Bond Elute SCX500MG: cationic ion-exchange resin, Varian)
  4. washThe SCX was washed with methanol
  5. washwith a mixed solution of chloroform/methanol (1/1), and elution
  6. distillationThe solvent was distilled off under reduced pressure

출처 및 근거

ORD 기록
ord-547fd898141640baa970d42228aef397
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517875B2

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