3-Methyl-2-thiophenecarboxaldehyde → (3-Methylthien-2-ylmethyl)-[4-(5-methylthio-3-pyridin-4-yl-1H-1,2,4-triazol-1-yl)phenyl]amine

HRID 1280544노트

반응식

HRID 1280544 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([S:13][CH3:14])=[N:11][C:10]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[N:9]2)=[CH:4][CH:3]=1.[CH3:21][C:22]1[CH:26]=[CH:25][S:24][C:23]=1[CH:27]=O.C([BH3-])#N.[Na+]>C(O)(=O)C.CO>[CH3:21][C:22]1[CH:26]=[CH:25][S:24][C:23]=1[CH2:27][NH:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([S:13][CH3:14])=[N:11][C:10]([C:15]3[CH:16]=[CH:17][N:18]=[CH:19][CH:20]=3)=[N:9]2)=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 799113-Methyl-2-thiophenecarboxaldehydeHCID 5003444Sodium cyanoborohydrideHCID 184258711-(4-aminophenyl)-5-methylthio-3-(4-pyridyl)-1H-1,2,4-triazole

생성물 1

HCID 18425879(3-Methylthien-2-ylmethyl)-[4-(5-methylthio-3-pyridin-4-yl-1H-1,2,4-triazol-1-yl)phenyl]amine

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 887Methanol용매

실험 절차

A stirred solution of 1-(4-aminophenyl)-5-methylthio-3-(4-pyridyl)-1H-1,2,4-triazole (Example 1) (100 mg, 0.35 mmol) and 3-methylthiophene-2-carboxaldehyde (44 mg, 0.35 mmol) in 5% acetic acid in MeOH (4 mL) at room temperature was treated with sodium cyanoborohydride (55 mg, 0.88 mmol) and the reaction mixture was further stirred at room temperature for 48 h. The reaction mixture was concentrated, diluted with EtOAc, washed with NaHCO3 solution, brine and dried (MgSO4). The residue obtained on concentration was flash chromatographed on silica gel and eluted with a gradient of dichloromethane/acetone (9/1 to 3/1). The title compound was obtained as a white solid (85 mg).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. additiondiluted with EtOAc
  3. washwashed with NaHCO3 solution, brine
  4. dry with materialdried (MgSO4)
  5. customThe residue obtained on concentration
  6. customchromatographed on silica gel
  7. washeluted with a gradient of dichloromethane/acetone (9/1 to 3/1)

출처 및 근거

ORD 기록
ord-34d645a9fa704ad29676d2a9f47237ce
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06451820B1

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