1-Phenethylamine → 3-(1-Phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyridin-2(3H)-one

HRID 1014716노트

반응식

HRID 1014716 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH3:10])[C:5]([N+:17]([O-])=O)=[CH:4][CH:3]=1.Cl[C:21]1[C:26]([N+]([O-])=O)=[CH:25][CH:24]=[C:23](Cl)[N:22]=1.C(N(C(C)C)CC)(C)C.[C:40]1(C(N)C)C=C[CH:43]=[CH:42][CH:41]=1.[O:49]1CCC[CH2:50]1>>[C:11]1([CH:9]([N:8]2[C:6]3=[N:7][C:2]([C:43]4[CH:42]=[CH:41][CH:40]=[C:21]5[C:26]=4[CH:25]=[CH:24][CH:23]=[N:22]5)=[CH:3][CH:4]=[C:5]3[NH:17][C:50]2=[O:49])[CH3:10])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

참가 물질

6

반응물 5

HCID 74081-PhenethylamineHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 852392,6-Dichloro-3-nitropyridineHCID 433303216-chloro-3-nitro-N-(1-phenylethyl)pyridin-2-amine

생성물 1

HCID 249846803-(1-Phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyridin-2(3H)-one수율 78%

반응 조건

온도
-78 °C

실험 절차

6-Chloro-3-nitro-N-(1-phenylethyl)pyridin-2-amine. To a solution of 2,6-dichloro-3-nitropyridine (2.0 g, 10.4 mmol) in tetrahydrofuran (18 mL) at −78° C. was added diisopropylethylamine (2.17 mL, 12.4 mmol) and 1-phenylethanamine (1.51 g, 12.4 mmol). The reaction was maintained at −78° C. for 2 h and then allowed to slowly warm to room temperature overnight. Solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography to afford the title compound (2.24 g, 78% yield). 1H NMR (400 MHz, DMSO-d6) δ 8.68 (d, J=7.5, 1H), 8.42 (d, J=8.5, 1H), 7.45 (d, J=7.5, 2H), 7.34 (t, J=7.5, 2H), 7.25 (t, J=7.5, 1H), 6.80 (d, J=8.5, 1H), 5.36 (app quint, J=7, 1H), 1.57 (d, J=7, 3H).

후처리

  1. temperatureto slowly warm to room temperature overnight
  2. customSolvent was removed under reduced pressure
  3. customthe crude product was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-6ff5800ff6254a87b7f2038ae20ef298
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07981893B2

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