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

HRID 1014697ノート

反応式

HRID 1014697 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
120 °C

実験手順

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]+

後処理

  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

出典と根拠

ORDレコード
ord-1dba2384092e466082a40a1618a52903
出典データセット
uspto-grants-2011_07
特許番号
US07981893B2

反応ノート

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