Octanoyl chloride → 4''-[3-Butyl-5-oxo-1-(2-trifluoromethyl-phenyl)-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid octanoyl-amide

HRID 36200

반응식

[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[S:34](=[O:37])(=[O:36])[NH2:35])=[CH:24][CH:23]=2)[C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[N:9]=1)[CH2:2][CH2:3][CH3:4].[C:38](Cl)(=[O:46])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45]>>[CH2:1]([C:5]1[N:6]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[S:34](=[O:37])(=[O:36])[NH:35][C:38](=[O:46])[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[CH:24][CH:23]=2)[C:7](=[O:20])[N:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]([F:19])([F:18])[F:17])[N:9]=1)[CH2:2][CH2:3][CH3:4]

참가 물질

반응물 2

HCID 8124Octanoyl chloride

HCID 103469025-n-Butyl-2,4-dihydro-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

생성물 1

HCID 100550964''-[3-Butyl-5-oxo-1-(2-trifluoromethyl-phenyl)-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid octanoyl-amide수율 37%

실험 절차

By the procedure of Example 13, Step C, 5-n-butyl-2,4-dihydro-4-[(2'-sulfamoylbiphenyl-4-yl)methyl]-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one (from Example 16, Step C) was reacted with octanoyl chloride. Flash chromatography of the crude product twice on silica gel (gradient elution with 0.3-3% and 0.5-2% MeOH in CH2Cl2) gave a 37% yield of the title compound as a gum, homogeneous by TLC in 19:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 657 (M+1)+. 400 MHz NMR CDCl3) δ0.81 (t, 3H), 0.89 (t, 3H), 1.1-1.3 (m, 8H), 1.39 (m, 4H), 1.66 (m, 2H), 1.88 (t, 2H), 2.55 (t, 2H), 4.92 (s, 2H), 7.26, (d, 2H), 7.35 (d, 2H), 7.5-7.7 (m, 6H), 7.78 (d, 1H), 8.20 (br s, 1H), 8.28 (d, 1H).

출처 및 근거

ORD 기록: ord-dcaf0765e43a4e019dd5ae7562f5e0a8
출처 데이터셋: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US05411980

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