(R)-3-(4-Bromo-benzyl)-1-(3,5-dichloro-phenyl)-3-methyl-1H-imidazo[1,2-a]imidazol-2-one → (R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-imidazo[1,2-a)-imidazol-2-one

HRID 23839노트

반응식

HRID 23839 반응식
Br[C:2]1[CH:26]=[CH:25][C:5]([CH2:6][C@@:7]2([CH3:24])[N:11]3[CH:12]=[CH:13][N:14]=[C:10]3[N:9]([C:15]3[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=3)[C:8]2=[O:23])=[CH:4][CH:3]=1.[C:27]([Cu])#[N:28]>CN(C=O)C>[C:27]([C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C@@:7]2([CH3:24])[N:11]3[CH:12]=[CH:13][N:14]=[C:10]3[N:9]([C:15]3[CH:20]=[C:19]([Cl:21])[CH:18]=[C:17]([Cl:22])[CH:16]=3)[C:8]2=[O:23])=[CH:25][CH:26]=1)#[N:28]

참가 물질

4

반응물 2

HCID 9911635(R)-3-(4-Bromo-benzyl)-1-(3,5-dichloro-phenyl)-3-methyl-1H-imidazo[1,2-a]imidazol-2-oneHCID 178418546HCID 178418546, 화합물

생성물 1

HCID 59923742(R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-imidazo[1,2-a)-imidazol-2-one수율 77.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
140 °C

실험 절차

(R)-3-(4-Bromobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-imidazo[1,2-α]-imidazol-2-one (13.5 g, 29.9 mmol) was dissolved in anhydrous DMF (70 mL) and CuCN (3.22 g, 35.9 mmol) was added. The reaction mixture was heated to 140° C. under argon for 40 h. When the reaction was complete, the solvent was removed under reduced pressure and the residue was diluted with CH2Cl2. The organic solution was washed four times alternately with 5% aqueous pyridine then water. The organic layer was dried over Na2SO4 and filtered through a diatomaceous earth pad. The filtrate was concentrated and purified by silica gel column chromatography using a mixture of CH2Cl2-hexane (10:1) as an eluent to afford 9.19 g of (R)-3-(4-cyanobenzyl)-1-(3,5-dichlorophenyl)-3-methyl-imidazo[1,2-a)-imidazol-2-one.

후처리

  1. customthe solvent was removed under reduced pressure
  2. additionthe residue was diluted with CH2Cl2
  3. washThe organic solution was washed four times alternately with 5% aqueous pyridine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered through a diatomaceous earth pad
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. additiona mixture of CH2Cl2-hexane (10:1) as an eluent

출처 및 근거

ORD 기록
ord-1ee585fcc3c146aba734715a5c383c6d
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852748B1

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