HCID 10054925, compound → HCID 10077491, compound

HRID 1198681Notes

Reaction equation

HRID 1198681 reaction equation
[C:1]([O:5][C:6]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][N:25]2[C:29]([CH2:30][CH2:31][CH2:32][CH3:33])=[N:28][N:27]([C:34]3[CH:39]=[C:38]([N+:40]([O-])=O)[CH:37]=[CH:36][C:35]=3[Cl:43])[C:26]2=[O:44])=[CH:20][CH:19]=1)(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]>[Pt]=O.C(OCC)(=O)C>[NH2:40][C:38]1[CH:37]=[CH:36][C:35]([Cl:43])=[C:34]([N:27]2[C:26](=[O:44])[N:25]([CH2:24][C:21]3[CH:20]=[CH:19][C:18]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=4[S:9](=[O:11])(=[O:10])[NH:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])=[CH:23][CH:22]=3)[C:29]([CH2:30][CH2:31][CH2:32][CH3:33])=[N:28]2)[CH:39]=1

Participants

4

Reactant 1

HCID 10054925HCID 10054925, compound

Product 1

HCID 10077491HCID 10077491, compoundYield 63.7%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 128 mg (0.2 mmol) of 4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-biphenyl-4-yl]methyl]-5-n-butyl-2-(2-chloro-5-nitrophenyl)-2,4-dihydro-3H -1,2,4-triazol-3-one (from Example 24), 10 mg of 10% platinum oxide on carbon, and 2 mL of ethyl acetate was stirred under a hydrogen atmosphere (balloon) for 4 hours. The mixture was then filtered through Celite, and the product was chromatographed on a column of silica gel (gradient elution with 0.5-5% methanol in CH2Cl2) to yield 78 mg of the title compound as a white solid, mp 185°-188° C.; nearly homogeneous by TLC (9:1 CH2Cl2 --MeOH).

Workup

  1. filtrationThe mixture was then filtered through Celite
  2. customthe product was chromatographed on a column of silica gel (gradient elution with 0.5-5% methanol in CH2Cl2)

Sources & evidence

ORD record
ord-07fb8359ea814c11981fba74a7fdef8e
Source dataset
uspto-grants-1994_01
Patent number
US05281614

Reaction notes

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