1,1'-Carbonyldiimidazole → 9-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-7H-purin-8(9H)-one

HRID 1363247노트

반응식

HRID 1363247 반응식
[Si:1]([O:18][C@H:19]1[C:28]2[C:23](=[CH:24][C:25]([F:29])=[CH:26][CH:27]=2)[C@H:22]([NH:30][C:31]2[C:36]([NH2:37])=[CH:35][N:34]=[C:33]([N:38]3[C:42]4[CH:43]=[C:44]([F:47])[CH:45]=[CH:46][C:41]=4[N:40]=[CH:39]3)[N:32]=2)[CH2:21][CH2:20]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1N=CN([C:53](N2C=NC=C2)=[O:54])C=1>C1COCC1>[Si:1]([O:18][C@H:19]1[C:28]2[C:23](=[CH:24][C:25]([F:29])=[CH:26][CH:27]=2)[C@H:22]([N:30]2[C:53](=[O:54])[NH:37][C:36]3[C:31]2=[N:32][C:33]([N:38]2[C:42]4[CH:43]=[C:44]([F:47])[CH:45]=[CH:46][C:41]=4[N:40]=[CH:39]2)=[N:34][CH:35]=3)[CH2:21][CH2:20]1)([C:14]([CH3:16])([CH3:15])[CH3:17])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

4

반응물 2

HCID 682631,1'-CarbonyldiimidazoleHCID 59846398N4-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)pyrimidine-4,5-diamine

생성물 1

HCID 598463719-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-7H-purin-8(9H)-one수율 83.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N4-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)pyrimidine-4,5-diamine (490 mg, 0.751 mmol, 1 equiv) was dissolved in anhydrous THF (15 mL) and CDI (737 mg, 4.54 mmol, 7 equiv) was added. The reaction was stirred at RT under argon overnight. The solvent was removed by evaporation. The residue was dissolved in EtOAc (30 mL) and washed with saturated NaHCO3, water and brine, dried (Na2SO4). The organic layer was evaporated to dryness. The residue was applied to ISCO (12 g column, MeOH—CH2Cl2 0-2%) to give a white solid product (420 mg, 82%). MS (ESI): 673.3

후처리

  1. customThe solvent was removed by evaporation
  2. dissolutionThe residue was dissolved in EtOAc (30 mL)
  3. washwashed with saturated NaHCO3, water and brine
  4. dry with materialdried (Na2SO4)
  5. customThe organic layer was evaporated to dryness

출처 및 근거

ORD 기록
ord-e27c0e87768c4ddf841637db9f15d25f
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07884109B2

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