Chloroacetonitrile → 2-(4-(Quinazolin-4-yl)piperazin-1-yl)acetonitrile

HRID 600472ノート

反応式

HRID 600472 の反応式
[N:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[CH:9][N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[CH3:17][CH2:18][N:19](CC)CC.ClCC#N>C1COCC1>[N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([N:1]2[CH2:6][CH2:5][N:4]([CH2:17][C:18]#[N:19])[CH2:3][CH2:2]2)=[N:8][CH:9]=1

参加物

5

反応物 3

HCID 7856ChloroacetonitrileHCID 8471TriethylamineHCID 18585334-Piperazin-1-ylquinazoline

生成物 1

HCID 552058602-(4-(Quinazolin-4-yl)piperazin-1-yl)acetonitrile収率 73.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 4-(piperazin-1-yl)quinazoline (1.8 g, 8.3 mmol) in THF (50 mL) was added NEt3 (20 mL, 150 mmol) and chloroacetonitrile (12 mL, 190 mmol) and the reaction was stirred 16 h. The reaction mixture was quenched with 50% saturated aqueous NaHCO3 and extracted with EtOAc (3×200 mL). The combined organics were purified by silica gel chromatography (50% EtOAc/hexanes to 80% EtOAc/hexanes) to yield 55 (1.6 g, 6.1 mmol, 73%) as an viscous yellow oil. 1H NMR: (500 MHz, CDCl3) δ 8.74 (s, 1H), 8.06 (d, J=8.6 Hz, 1H), 7.90 (d, J=8.5 Hz, 1H), 7.82-7.55 (m, 1H), 7.54-7.50 (m, 1H), 3.94-3.88 (m, 4H), 3.63 (s, 2H), 2.86-2.81 (m, 4H); LC/MS: (ES+) m/z (M+H)+=254; HPLC Rt=0.71 min., column O.

後処理

  1. customThe reaction mixture was quenched with 50% saturated aqueous NaHCO3
  2. extractionextracted with EtOAc (3×200 mL)
  3. customThe combined organics were purified by silica gel chromatography (50% EtOAc/hexanes to 80% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-70497f208cad4104bc1f2bbf2ae09378
出典データセット
uspto-grants-2011_03
特許番号
US07902204B2

反応ノート

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