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2-(2-Bromoethoxy)-4-nitrobenzonitrile → 2-(2-(2-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ylamino)ethylamino)ethoxy)-4-nitrobenzonitrile

HRID 474264
ノート
印刷プレビュー

反応式

HRID 474264 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([NH:18][CH2:19][CH2:20][NH2:21])[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[CH2:23][CH2:24][O:25][C:26]1[CH:33]=[C:32]([N+:34]([O-:36])=[O:35])[CH:31]=[CH:30][C:27]=1[C:28]#[N:29]>CN(C=O)C>[Cl:1][C:2]1[N:3]=[C:4]([NH:18][CH2:19][CH2:20][NH:21][CH2:23][CH2:24][O:25][C:26]2[CH:33]=[C:32]([N+:34]([O-:36])=[O:35])[CH:31]=[CH:30][C:27]=2[C:28]#[N:29])[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
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 666658762-(2-Bromoethoxy)-4-nitrobenzonitrileHCID 86668112N1-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)ethane-1,2-diamine

生成物 1

HCID 866681112-(2-(2-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ylamino)ethylamino)ethoxy)-4-nitrobenzonitrile収率 21.7%

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)ethane-1,2-diamine {Preparation Sc Step (1), 1.0 g, 3.265 mmol} in DMF (5 mL) was added TEA (0.495 g, 4.89 mmol) followed by 2-(2-bromoethoxy)-4-nitrobenzonitrile (Preparation N, 1.05 g, 3.91 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 taken 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, 10% methanol in chloroform) to get 2-(2-(2-(2-chloro-7-(4-fluorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-ylamino)ethylamino)ethoxy)-4-nitrobenzonitrile (0.35 g, 21.7%) as a light yellow solid. LC-MS (M+H)+=497.2. 1H NMR (400 MHz, CDCl3) δ ppm 7.93-7.91 (1H, d, J=6.8 Hz), 7.90 (1H, s), 7.86-7.85 (1H, m), 7.12-7.00 (2H, m), 6.98-6.96 (2H, m), 5.30 (1H, br s), 4.34-4.32 (2H, m), 4.26-4.24 (1H, m), 3.70-3.66 (2H, m), 3.21-3.19 (2H, m), 3.04-3.02 (2H, m), 2.78-2.63 (3H, m), 1.99-1.98 (1H, m).

後処理

  1. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-283b586d9fb749a78ebe23db805d2259
出典データセット
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08637523B2

反応ノート

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