Dimethyl Sulfoxide → N-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-5-nitropyrimidin-4-amine

HRID 1363245노트

반응식

HRID 1363245 반응식
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[N:15]=[C:14](SC#N)[C:13]([N+:19]([O-:21])=[O:20])=[CH:12][N:11]=3)[C:6]=2[CH:22]=1.[Si:23]([O:40][C@H:41]1[C:50]2[C:45](=[CH:46][C:47]([F:51])=[CH:48][CH:49]=2)[C@H:44]([NH2:52])[CH2:43][CH2:42]1)([C:36]([CH3:39])([CH3:38])[CH3:37])([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.CCN(C(C)C)C(C)C.CS(C)=O>C1COCC1>[Si:23]([O:40][C@H:41]1[C:50]2[C:45](=[CH:46][C:47]([F:51])=[CH:48][CH:49]=2)[C@H:44]([NH:52][C:14]2[C:13]([N+:19]([O-:21])=[O:20])=[CH:12][N:11]=[C:10]([N:7]3[C:6]4[CH:22]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=4[N:9]=[CH:8]3)[N:15]=2)[CH2:43][CH2:42]1)([C:36]([CH3:39])([CH3:37])[CH3:38])([C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1)[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 597049556-Fluoro-1-(5-nitro-4-thiocyanatopyrimidin-2-yl)-1H-benzo[d]imidazoleHCID 59846380(1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-amine

생성물 1

HCID 59846358N-((1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-yl)-2-(6-fluoro-1H-benzo[d]imidazol-1-yl)-5-nitropyrimidin-4-amine수율 65.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

6-Fluoro-1-(5-nitro-4-thiocyanatopyrimidin-2-yl)-1H-benzo[d]imidazole (498 mg, 1.57 mmol, 1.1 equiv) was added to a solution of (1R,4R)-4-(tert-butyldiphenylsilyloxy)-7-fluoro-1,2,3,4-tetrahydronaphthalen-1-amine (600 mg, 1.43 mmol, 1 equiv) in THF (20 mL) containing DIEA (1.5 mL), followed by adding 2 mL of DMSO. The resulted red solution was stirred at RT for 16 h. THF was evaporated off The residue was dissolved in EtOAc, washed with water and brine, dried (Na2SO4). The organic layer was evaporated to dryness. The residue was purified on ISCO (12 g column, MeOH—CH2Cl2 0-5%) to give a yellow solid product (633 mg, 65%). MS (ESI): 677.3.

후처리

  1. customTHF was evaporated off The residue
  2. dissolutionwas dissolved in EtOAc
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customThe organic layer was evaporated to dryness
  6. customThe residue was purified on ISCO (12 g column, MeOH—CH2Cl2 0-5%)

출처 및 근거

ORD 기록
ord-243f50c619b3441baa35016ac8c21433
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07884109B2

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