Propyl isocyanate → 4''-{3-Butyl-1-[2-chloro-5-(3-propyl-ureido)-phenyl]-5-oxo-1,5-dihydro-[1,2,4]triazol-4-ylmethyl}-biphenyl-2-sulfonic acid 2-chloro-benzoylamide

HRID 36255

반응식

HRID 36255 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.[CH2:45]([N:48]=[C:49]=[O:50])[CH2:46][CH3:47]>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:49]([NH:48][CH2:45][CH2:46][CH3:47])=[O:50])[CH:3]=[CH:4][C:5]=2[Cl:44])[N:9]=1)[CH2:41][CH2:42][CH3:43]

참가 물질

5

반응물 2

HCID 61033Propyl isocyanateHCID 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 102594114''-{3-Butyl-1-[2-chloro-5-(3-propyl-ureido)-phenyl]-5-oxo-1,5-dihydro-[1,2,4]triazol-4-ylmethyl}-biphenyl-2-sulfonic acid 2-chloro-benzoylamide수율 61%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 1049Pyridine용매

실험 절차

At room temperature, under N2, a solution of 34 mg (0.052 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), 6.4 mg (0.052 mmole) of DMAP, 23 mg (0.26 mmole) of propyl isocyanate, and 1 mL of pyridine was stirred overnight. After quenching with 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 23 mg (61%) of the desired compound as a white solid, mp >208° C. (gradual), homogeneous by TLC (9:1 MeOH/CH2Cl2), mass spectrum (FAB) m/e 773 (M+K)+.

후처리

  1. customAfter quenching with 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-432505845fda4bc2b35b9c1ceb2e42c0
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05411980

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