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

Reaction equation

HRID 36255 reaction equation
[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]

Participants

5

Reactant 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

Product 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-benzoylamideYield 61%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

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)+.

Workup

  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)

Sources & evidence

ORD record
ord-432505845fda4bc2b35b9c1ceb2e42c0
Source dataset
uspto-grants-1995_05
Patent number
US05411980

Linked notes

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