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 1363245ノート

反応式

HRID 1363245 の反応式
[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

参加物

6

反応物 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

生成物 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-amine収率 65.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-243f50c619b3441baa35016ac8c21433
出典データセット
uspto-grants-2011_02
特許番号
US07884109B2

反応ノート

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