Propyl chloroformate → (3-{3-Butyl-4-[2''-(2-chloro-benzoylsulfamoyl)-biphenyl-4-ylmethyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}-4-chloro-phenyl)-carbamic acid propyl ester

HRID 36254

반응식

HRID 36254 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:44])=[C:6]([N:8]2[C:12](=[O:13])[N:11]([CH2:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[S:27](=[O:39])(=[O:38])[NH:28][C:29](=[O:37])[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=4[Cl:36])=[CH:17][CH:16]=3)[C:10]([CH2:40][CH2:41][CH2:42][CH3:43])=[N:9]2)[CH:7]=1.Cl[C:46]([O:48][CH2:49][CH2:50][CH3:51])=[O:47]>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[CH2:40]([C:10]1[N:11]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[S:27](=[O:38])(=[O:39])[NH:28][C:29](=[O:37])[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=3[Cl:36])=[CH:19][CH:20]=2)[C:12](=[O:13])[N:8]([C:6]2[CH:7]=[C:2]([NH:1][C:46]([O:48][CH2:49][CH2:50][CH3:51])=[O:47])[CH:3]=[CH:4][C:5]=2[Cl:44])[N:9]=1)[CH2:41][CH2:42][CH3:43]

참가 물질

5

반응물 2

HCID 7998Propyl chloroformateHCID 100321934''-[1-(5-Amino-2-chloro-phenyl)-3-butyl-5-oxo-1,5-dihydro-[1,2,4]triazol-4-ylmethyl]-biphenyl-2-sulfonic acid 2-chloro-benzoylamide

생성물 1

HCID 10010207(3-{3-Butyl-4-[2''-(2-chloro-benzoylsulfamoyl)-biphenyl-4-ylmethyl]-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl}-4-chloro-phenyl)-carbamic acid propyl ester수율 65.7%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

At room temperature, under N2, a solution of 20 mg (0.031 mmole) of 2-(5-amino-2-chlorophenyl)-5-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (from Example 60), 3.8 mg (0.031 mmole) of DMAP, 18.9 mg (0.154 mmole) of propyl chloroformate, and 1 mL pyridine was stirred overnight. After quenching with methanol and water, the organic material was extracted with EtOAc, washed with water and brine, and dried over sodium sulfate. The crude product obtained after filtration and removal of volatiles was flash chromatographed over silica gel (gradient elution with 0.5-5% MeOH/CH2Cl2) to give 15 mg (65%) of the desired compound as a white solid, mp >119° C. (gradual), homogeneous by TLC (9:1 MeOH/CH2Cl2), mass spectrum (FAB) m/e 736 (M+1)+.

후처리

  1. customAfter quenching with methanol and water
  2. extractionthe organic material was extracted with EtOAc
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customThe crude product obtained
  6. filtrationafter filtration and removal of volatiles
  7. customchromatographed over silica gel (gradient elution with 0.5-5% MeOH/CH2Cl2)

출처 및 근거

ORD 기록
ord-2ed56beeec4340a8b46c668a07cf5fec
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05411980

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