Sodium hydride → 5-chloro-1-(2-methoxy-ethoxymethyl)-6-pyrrolidin-1-yl-1H-benzoimidazole

HRID 538125

반응식

HRID 538125 반응식
[Cl:1][C:2]1[C:3]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][C:5]2[N:9]=[CH:8][NH:7][C:6]=2[CH:10]=1.[H-].[Na+].Cl[CH2:19][O:20][CH2:21][CH2:22][O:23][CH3:24]>C1COCC1>[Cl:1][C:2]1[C:3]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[CH:4][C:5]2[N:9]([CH2:19][O:20][CH2:21][CH2:22][O:23][CH3:24])[CH:8]=[N:7][C:6]=2[CH:10]=1

참가 물질

5

반응물 3

HCID 24758Sodium hydrideHCID 775901-(Chloromethoxy)-2-methoxyethaneHCID 669374346-chloro-5-pyrrolidin-1-yl-1H-benzoimidazole

생성물 1

HCID 669372385-chloro-1-(2-methoxy-ethoxymethyl)-6-pyrrolidin-1-yl-1H-benzoimidazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

To a mixture of 6-chloro-5-pyrrolidin-1-yl-1H-benzoimidazole (0.443 g, 2.00 mmol) and THF (5 mL) was added NaH (96.0 mg, 60% dispersion in mineral oil, 2.40 mmol) at 0° C. After stirring the reaction mixture for 30 min at 0° C., 1-chloromethoxy-2-methoxy-ethane (0.299 g, 2.40 mmol) was added and the mixture was stirred for 18 h. The reaction mixture was quenched with water and the aqueous layer was extracted with EtOAc (3×50 mL). The combined organic layers were washed with brine (2×20 mL), dried, filtered, and concentrated under reduced pressure. The residue was purified (FCC) (0-10% MeOH/DCM) to yield the titled compound as a mixture of regioisomers (0.240 g, 39%) with a purity of 90%. MS (ESI/CI): mass calcd. for C15H20ClN3O2, 309.1; m/z found, 310.1 [M+H]+.

후처리

  1. stirringthe mixture was stirred for 18 h
  2. customThe reaction mixture was quenched with water
  3. extractionthe aqueous layer was extracted with EtOAc (3×50 mL)
  4. washThe combined organic layers were washed with brine (2×20 mL)
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified (FCC) (0-10% MeOH/DCM)

출처 및 근거

ORD 기록
ord-48292d782959418c9914f84482cbc5be
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08865713B2

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