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

HRID 388120노트

반응식

HRID 388120 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-c55471e35e644277b9655063147e970e
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372976B2

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