Hydrochloric Acid → (E)-2-(2,4-Difluorostyryl)-1-(2-pyridyl)-1H-benzimidazole hydrochloride

HRID 50886노트

반응식

HRID 50886 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]=[C:25]([F:27])[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]=[C:25]([F:27])[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 9796241(E)-1-(2-pyridyl)-2-styryl-1H-benzimidazoleHCID 11159992HCID 11159992, 화합물

생성물 1

HCID 22736765(E)-2-(2,4-Difluorostyryl)-1-(2-pyridyl)-1H-benzimidazole hydrochloride

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a solution of (E)-2,4-difluorocinnamic acid (331 mg, 1.8 mmol) in benzene (10 ml) was added thionyl chloride (0.5 ml) and the mixture was heated to reflux for 60 min. Volatiles were removed by evaporation to give crude (E)-2,4-difluorocinnamoyl chloride. Free base of the titled compound was prepared from N-(2-pyridyl)-o-phenylenediamine (250 mg, 1.4 mmol) and (E)-2,4-difluorocinnamoyl chloride obtained as above 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: 369.80; mp: 194.8-196.8° C.; 1H-NMR (DMSO) δ: 8.84-8.79 (1H, m), 8.30-8.08 (2H, m), 7.96-7.82 (3H, m), 7.78-7.69 (1H, m), 7.61-7.13 (6H, m).

후처리

  1. customobtained as
  2. concentrationConcentration and recrystallization from ethyl acetate/ethanol

출처 및 근거

ORD 기록
ord-1e222c9a98ae461593bad479ba340613
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713482B2

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