HCID 10484475, compound → HCID 10258462, compound

HRID 1198710Notes

Reaction equation

HRID 1198710 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])=[C:20]([F:45])[CH:19]=1)(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pt]=O.C(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:22]=[CH:23][C:18]([C:13]4[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=4[S:9](=[O:10])(=[O:11])[NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:19][C:20]=3[F:45])[C:29]([CH2:30][CH2:31][CH2:32][CH3:33])=[N:28]2)[CH:39]=1

Participants

5

Reactant 2

HCID 10484475HCID 10484475, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 10258462HCID 10258462, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 313 mg (0.475 mmol) of 4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]-3-fluorobiphenyl-4-yl]methyl]-5-n-butyl-2-(2-chloro-5-nitrophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one (from Step B), 10 mg of platinum oxide, and 4 mL of ethanol was shaken with hydrogen at approximately 3 atm for 2.5 hours. The mixture was filtered through Celite, and the filtrate was concentrated to dryness. The residue was flash chromatographed on about 60 cc of silica gel (gradient elution with 0.5-2% MeOH in CH2Cl2) to give a 57% yield of the title compound as a cream-colored solid, mp 208°-210° C.; homogeneous by TLC in 95:5 CH2Cl2 --MeOH.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated to dryness
  3. customchromatographed on about 60 cc of silica gel (gradient elution with 0.5-2% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-ad0fa4ffb8604171a531e5eb0d7e5436
Source dataset
uspto-grants-1994_01
Patent number
US05281614

Reaction notes

Loading…