Methanol → 1-(cyclopropylmethyl)-2-[(5-ethoxy-2-pyridinyl)methyl]-1H-benzimidazole-5-carbonitrile

HRID 1796483노트

반응식

HRID 1796483 반응식
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:14]#[N:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][N:18]=2)[CH2:3][CH2:2]1.CO[Na].CO.[CH2:29](I)[CH3:30]>CS(C)=O.O>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([C:14]#[N:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:29][CH3:30])=[CH:19][N:18]=2)[CH2:3][CH2:2]1

참가 물질

7

반응물 4

HCID 887MethanolHCID 6340IodoethaneHCID 221812711-(cyclopropylmethyl)-2-[(5-hydroxy-2-pyridinyl)methyl]-1H-benzimidazole-5-carbonitrileHCID 178418582HCID 178418582, 화합물

생성물 1

HCID 221812731-(cyclopropylmethyl)-2-[(5-ethoxy-2-pyridinyl)methyl]-1H-benzimidazole-5-carbonitrile수율 64.1%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

To a solution of 1-(cyclopropylmethyl)-2-[(5-hydroxy-2-pyridinyl)methyl]-1H-benzimidazole-5-carbonitrile (120 mg, 0.394 mmol) in DMSO (1 mL) was added MeONa (25% in MeOH, 0.47 mmol). After being stirred at room temperature for 30 min, MeOH was removed in vacuo and EtI (0.47 mmol) was added, and the resulting mixture was stirred at room temperature overnight. The solution was diluted with H2O (10 mL), extracted with EtOAc (2×20 mL), washed with H2O (2×10 mL), and lastly dried over MgSO4. The residue obtained after evaporation was purified by silica gel column chromatography to give the pure product as an oil (84 mg, 64%). 1H NMR (400 MHz, CDCl3): δ 8.19 (d, J=3.0 Hz, 1H), 8.04 (s, 1H), 7.49 (d, J=8.4 Hz, 1H), 7.42 (d, J=8.4 Hz, 1H), 7.24 (d, J=8.8 Hz, 1H), 7.13 (dd, J=10.0 Hz, J=2.8 Hz, 1H), 4.47 (s, 2H), 4.15 (d, J=6.8 Hz, 2H), 4.04 (q, J=7.0 Hz, 2H), 1.41 (t, J=7.0 Hz, 3H), 1.14–1.08 (m, 1H), 0.60–0.54 (m, 2H), 0.36–0.30 (m, 2H). MS (ES) (M+H)+=333.

후처리

  1. additionwas added
  2. stirringthe resulting mixture was stirred at room temperature overnight
  3. extractionextracted with EtOAc (2×20 mL)
  4. washwashed with H2O (2×10 mL)
  5. dry with materiallastly dried over MgSO4
  6. customThe residue obtained
  7. customafter evaporation
  8. customwas purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-d67c2d6bab5c4f0a9b0b876c537611dc
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07030139B2

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