Tetrahydrofuran → 2-(3-Chloro-4-cyanophenyl)-3-(4-fluorophenyl)-2,3,3a,4-tetrahydrochromeno[4,3-c]pyrazole-7-carboxylic acid

반응식

[F:1][C:2]1[CH:23]=[CH:22][C:5]([CH:6]=[C:7]2[C:16](=O)[C:15]3[C:10](=[CH:11][C:12]([C:18]([O:20]C)=[O:19])=[CH:13][CH:14]=3)[O:9][CH2:8]2)=[CH:4][CH:3]=1.Cl.[Cl:25][C:26]1[CH:33]=[C:32]([NH:34][NH2:35])[CH:31]=[CH:30][C:27]=1[C:28]#[N:29].O1CCCC1>>[Cl:25][C:26]1[CH:33]=[C:32]([N:34]2[CH:6]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:23][CH:22]=3)[CH:7]3[CH2:8][O:9][C:10]4[CH:11]=[C:12]([C:18]([OH:20])=[O:19])[CH:13]=[CH:14][C:15]=4[C:16]3=[N:35]2)[CH:31]=[CH:30][C:27]=1[C:28]#[N:29]

참가 물질

반응물 3

HCID 8028Tetrahydrofuran

HCID 221118492-Chloro-4-hydrazinylbenzonitrile hydrochloride

HCID 66722965Methyl 3-(4-fluorobenzylidene)-4-oxochroman-7-carboxylate

생성물 1

HCID 667229232-(3-Chloro-4-cyanophenyl)-3-(4-fluorophenyl)-2,3,3a,4-tetrahydrochromeno[4,3-c]pyrazole-7-carboxylic acid수율 18%

실험 절차

The title compound was prepared from methyl 3-(4-fluorobenzylidene)-4-oxochroman-7-carboxylate; Preparation 30 (155 mg, 0.50 mmol) and 2-chloro-4-hydrazinylbenzonitrile hydrochloride; Preparation 1 (153 mg, 0.75 mmol) according to Method B and Method C. The crude product was purified by reverse-phase HPLC (acetonitrile/water/0.05% trifluoroacetic acid) to give 2-(3-chloro-4-cyanophenyl)-3-(4-fluorophenyl)-2,3,3a,4-tetrahydrochromeno[4,3-c]pyrazole-7-carboxylic acid (41 mg, 0.09 mmol, 18% yield). The title compound was largely present as (±)-(3SR,3aSR)-2-(3-chloro-4-cyanophenyl)-3-(4-fluorophenyl)-2,3,3a,4-tetrahydrochromeno[4,3-c]pyrazole-7-carboxylic acid. ES-MS m/z 448 (M+H).