HCID 19783221, compound → HCID 19783146, compound

HRID 257558Notes

Reaction equation

HRID 257558 reaction equation
[CH2:1]([C:5]1[C:9]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[S:23](=[O:35])(=[O:34])[NH:24][C:25](=[O:33])[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[Cl:32])=[CH:13][CH:12]=2)=[C:8]([C:36]([O:38][CH2:39][CH3:40])=[O:37])[N:7]([C:41]2[CH:46]=[C:45]([N+:47]([O-])=O)[CH:44]=[CH:43][C:42]=2[Cl:50])[N:6]=1)[CH2:2][CH2:3][CH3:4].[H][H]>[Pt]=O.C(O)C>[NH2:47][C:45]1[CH:44]=[CH:43][C:42]([Cl:50])=[C:41]([N:7]2[C:8]([C:36]([O:38][CH2:39][CH3:40])=[O:37])=[C:9]([CH2:10][C:11]3[CH:12]=[CH:13][C:14]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[S:23](=[O:34])(=[O:35])[NH:24][C:25](=[O:33])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=4[Cl:32])=[CH:15][CH:16]=3)[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[N:6]2)[CH:46]=1

Participants

5

Reactant 2

HCID 19783221HCID 19783221, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19783146HCID 19783146, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

A mixture of 450 mg (0.612 mmol) of ethyl 3-n-butyl-4-[[2'-[N-(2-chlorobenzoyl)sulfamoyl]biphenyl-4-yl]methyl]-1-(2-chloro-5-nitrophenyl)-1H-pyrazole-5-carboxylate (from Step H), 50 mg of platinum oxide and 80 mL of ethanol was shaken with hydrogen at 3-4 atm for 1.25 hours. The catalyst was removed by filtration through Celite, and the filtrate was concentrated in vacuo to yield 401 mg (93%) of the title compound as a tan solid, mp>75° C. (gradual); nearly homogeneous by TLC in 95:5 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 705 (M+1)+. 400 MHz 1H NMR (DMSO-d6) δ0.81 (t, J=7.4 Hz, 3H), 0.97 (t, J=7.1 Hz, 3H), 1.25 (m, 2H), 1.48 (m, 2H), 2.49 (t, 2H, partially obscured by DMSO peak), 4.0-4.2 (m, 4H), 5.5 (v br m, 2H), 6.64 (m, 2H), 7.1-7.4 (m, 8H), 7.47 (m, 2H), 7.6-7.75 (m, 2H), 8.16 (dd, J=8.0, 1.1 Hz, 1H).

Workup

  1. customThe catalyst was removed by filtration through Celite
  2. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-be857bdf7eb9462d9c838c3cf1e28961
Source dataset
uspto-grants-1993_11
Patent number
US05262412

Reaction notes

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