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

HRID 600472노트

반응식

HRID 600472 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-70497f208cad4104bc1f2bbf2ae09378
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07902204B2

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