Methyl iodide → 10-Chloro-2-cyclopentyl-4,4-diethyl-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one

HRID 2234505

반응식

HRID 2234505 반응식
[Cl:1][C:2]1[N:12]=[C:11]2[C:5]([NH:6][C:7](=[O:22])[C:8]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:9][N:10]2[CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][N:3]=1.[CH3:23]I.[H-].[Na+]>CC(N(C)C)=O>[Cl:1][C:2]1[N:12]=[C:11]2[C:5]([N:6]([CH3:23])[C:7](=[O:22])[C:8]([CH2:20][CH3:21])([CH2:18][CH3:19])[CH2:9][N:10]2[CH:13]2[CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:4][N:3]=1

참가 물질

5

반응물 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 8661759110-Chloro-2-cyclopentyl-4,4-diethyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one2회

생성물 1

HCID 8661756310-Chloro-2-cyclopentyl-4,4-diethyl-6-methyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one

시약·촉매·용매 1

HCID 31374Dimethylacetamide용매

반응 조건

온도
3 °C

실험 절차

To a stirred solution of 10-chloro-2-cyclopentyl-4,4-diethyl-2,6,9,11-tetrazabicyclo[5.4.0]undeca-7,9,11-trien-5-one (Intermediate 251; 2.5 g, 7.76 mmol) in DMA (50 mL) under nitrogen was added methyl iodide (0.627 mL, 10.0 mmol). The mixture was cooled on an ice/water bath to 3° C., and sodium hydride (60% mineral oil dispersion; 0.567 g, 11.8 mmol) added in one portion. The reaction mixture was stirred on the ice/water bath for 1 hour before warming to room temperature and the reaction stirred for 4 hours. The reaction mixture was evaporated to dryness to afford a black solid, which was quenched with saturated aqueous NH4Cl solution (50 mL), extracted with DCM (3×100 mL), dried and solvent removed in vacuo to yield a black solid which was purified on a silica column eluting with DCM. The obtained solid was added to a diethyl ether and sonicated and the resultant material filtered and dried to yield the title compound as an off white solid (2.1 g, 80%).

후처리

  1. temperaturebefore warming to room temperature
  2. customThe reaction mixture was evaporated to dryness
  3. customto afford a black solid, which
  4. customwas quenched with saturated aqueous NH4Cl solution (50 mL)
  5. extractionextracted with DCM (3×100 mL)
  6. customdried
  7. customsolvent removed in vacuo
  8. customto yield a black solid which
  9. customwas purified on a silica column
  10. washeluting with DCM
  11. additionThe obtained solid was added to a diethyl ether
  12. customsonicated
  13. filtrationthe resultant material filtered
  14. customdried

출처 및 근거

ORD 기록
ord-0bd533d5da72449e872b94fd260ba2aa
출처 데이터셋
uspto-grants-2010_05
특허 번호
US07709471B2

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