1,1'-Carbonyldiimidazole → 4-(3-(Cyclohexylmethyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-B]pyrazin-5-YL)benzamide

HRID 388104노트

반응식

HRID 388104 반응식
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:12][CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:9](=[O:11])[NH:10][C:5]2=[N:4][CH:3]=1.BrC1N=C([NH:26][CH2:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]2)C(N)=NC=1.C(N1C=CN=C1)(N1C=CN=C1)=[O:36]>C1COCC1.CN(C=O)C>[CH:13]1([CH2:12][N:8]2[C:6]3[C:5](=[N:4][CH:3]=[C:2]([C:31]4[CH:32]=[CH:33][C:28]([C:27]([NH2:26])=[O:36])=[CH:29][CH:30]=4)[N:7]=3)[NH:10][C:9]2=[O:11])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1

참가 물질

6

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 866263916-Bromo-1-(cyclohexylmethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-oneHCID 866263926-Bromo-N2-(cyclohexylmethyl)pyrazine-2,3-diamine

생성물 1

HCID 574013314-(3-(Cyclohexylmethyl)-2-oxo-2,3-dihydro-1H-imidazo[4,5-B]pyrazin-5-YL)benzamide수율 89%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

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온도
120 °C

실험 절차

6-Bromo-1-(cyclohexylmethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one. 6-Bromo-N2-(cyclohexylmethyl)pyrazine-2,3-diamine (4.85 g, 17.01 mmol) was dissolved in THF (50 mL), 1,1′-carbonyldiimidazole (3.45 g, 21.26 mmol) was added, and the reaction solution was divided into 4 different vials. Each fraction was heated in a Biotage Emrys Optimizer microwave reactor at 120° C. for 30 min. The reacted fractions were combined and condensed under reduced pressure. The crude material was dissolved in minimal DMF and precipitated with deionized water while sonicating. The filtered product was dried in a vacuum oven at 60° C. over night to afford the title compound (4.72 g, 89%). MS (ESI) m/z 311.3 [M]+, 313.5 [M+2]+

후처리

  1. customcondensed under reduced pressure
  2. customprecipitated with deionized water
  3. customwhile sonicating
  4. customThe filtered product was dried in a vacuum oven at 60° C. over night

출처 및 근거

ORD 기록
ord-8f81d0f7eefd487882cb0c339bbab86b
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372976B2

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