1-(2-(2-bromoethoxy)-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole → N1-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-N2-methyl-N2-(2-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)ethyl)ethane-1,2-diamine

HRID 474263ノート

反応式

HRID 474263 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([NH:18][CH2:19][CH2:20][NH:21][CH3:22])[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1.Br[CH2:24][CH2:25][O:26][C:27]1[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:28]=1[N:36]1[CH:40]=[N:39][C:38]([CH3:41])=[N:37]1>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:18][CH2:19][CH2:20][N:21]([CH3:22])[CH2:24][CH2:25][O:26][C:27]2[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:28]=2[N:36]2[CH:40]=[N:39][C:38]([CH3:41])=[N:37]2)[C:5]2[CH2:10][CH2:9][CH:8]([C:11]3[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=3)[C:6]=2[N:7]=1

参加物

4

反応物 2

HCID 666688591-(2-(2-bromoethoxy)-4-nitrophenyl)-3-methyl-1H-1,2,4-triazoleHCID 86668110N1-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-N2-methylethane-1,2-diamine

生成物 1

HCID 86668109N1-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-N2-methyl-N2-(2-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)ethyl)ethane-1,2-diamine収率 30.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of N1-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-N2-methylethane-1,2-diamine (0.2 g, 0.623 mmol) in DMF (3 mL) was added TEA (0.095 g, 0.935 mmol) followed by 1-(2-(2-bromoethoxy)-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole (Preparation J, 0.245 g, 0.233 mmol) at room temperature. The reaction mixture was stirred at rt for 18 h. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane (5 mL) and silica (1 g). The resultant slurry of the compound in silica was subjected to flash chromatography using a Teledyne Isco instrument (12 g RediSep silica column, with 10% methanol in chloroform) to get N1-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)-N2-methyl-N2-(2-(2-(3-methyl-1H-1,2,4-triazol-1-yl)-5-nitrophenoxy)ethyl)ethane-1,2-diamine (0.04 g, 13.12%) as a dark brown solid. LC-MS (M+H)+=567.2. 1H NMR (400 MHz, CDCl3) δ ppm 8.25 (1H, s), 7.14-7.08 (3H, m), 6.99-6.95 (2H, m), 6.41 (1H, s), 6.32 (1H, d, J=8.4 Hz), 4.39 (2H, br s), 4.14 (1H, t, J=8.8 Hz), 3.93-3.88 (4H, m), 3.22-3.09 (6H, m), 2.55-2.54 (1H, m), 2.46 (3H, s), 1.99-1.98 (1H, m).

後処理

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane (5 mL)

出典と根拠

ORDレコード
ord-9583646732b94feab096a2cede3d2952
出典データセット
uspto-grants-2014_01
特許番号
US08637523B2

反応ノート

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