Hydrochloric Acid → (E)-2-(2-Fluorostyryl)-1-(2-pyridyl)-1H-benzimidazole hydrochloride

HRID 50883노트

반응식

HRID 50883 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:14].[F:15][C:16]1[CH:26]=[CH:25][CH:24]=[CH:23][C:17]=1/[CH:18]=[CH:19]/[C:20]([Cl:22])=O.N1C=CC=CC=1N1C2C=CC=CC=2N=C1/C=C/C1C=CC=CC=1.Cl>CO>[ClH:22].[F:15][C:16]1[CH:26]=[CH:25][CH:24]=[CH:23][C:17]=1/[CH:18]=[CH:19]/[C:20]1[N:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N:14]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 752150N1-(pyridin-2-yl)benzene-1,2-diamineHCID 5706469(2E)-3-(2-Fluorophenyl)acryloyl chlorideHCID 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole

생성물 1

HCID 9906470(E)-2-(2-Fluorostyryl)-1-(2-pyridyl)-1H-benzimidazole hydrochloride

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Free base of the titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine and (E)-2-fluorocinnamoyl chloride (Amino, Y.; Kawada, K.; Toi, K.; Kumashiro, I.; Fukushima, K. Chem. Pharm. Bull, 1988, 36, 4426) according to the preparation of (E)-1-(2-pyridyl)-2-styryl-1H-benzimidazole (Example 1, method A). The free base was dissolved with a 10% methanol solution of hydrogen chloride (5 ml). Concentration and recrystallization from ethyl acetate/ethanol yielded the titled compound. MW: 351.81; mp: 226.0-228.0° C.; 1H-NMR (DMSO) δ: 8.92-8.87 (1H, m), 8.39-8.29 (1H, m), 8.29 (1H, d, J=16.1 Hz), 7.99-7.79 (4H, m), 7.70-7.51 (4H, m), 7.44-7.31 (3H, m).

후처리

  1. concentrationConcentration and recrystallization from ethyl acetate/ethanol

출처 및 근거

ORD 기록
ord-d129c2b05840490f94a91469e471a5fd
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713482B2

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