HCID 19076577, compound → HCID 19076557, compound

HRID 234502Notes

Reaction equation

HRID 234502 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][CH:15]=1)(=[O:13])=[O:12])[C:6](=[O:23])[C:5]2([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[Cl:38])[NH:24][C:25]([N:27]([CH2:30][CH3:31])[CH2:28][CH3:29])=[O:26].[H][H]>CCO.C1COCC1.[Ni]>[NH2:20][C:17]1[CH:18]=[CH:19][C:14]([S:11]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=3)[C:5]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[Cl:38])([NH:24][C:25]([N:27]([CH2:28][CH3:29])[CH2:30][CH3:31])=[O:26])[C:6]2=[O:23])(=[O:13])=[O:12])=[CH:15][CH:16]=1

Participants

6

Reactant 2

HCID 19076577HCID 19076577, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19076557HCID 19076557, compound

Reagents, catalysts & solvents 3

HCID 935NickelCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

7.6 g of the compound obtained in EXAMPLE 12 in 100 ml of EtOH and 50 ml of THF are reduced with hydrogen under a pressure of 50 bar for 6 hours at RT, in the presence of 2 g of Raney nickel. The mixture is filtered on C elite and the filtrate is evaporated under vacuum. The residue is chromatographed on silica using a DCM/AcOEt mixture (95/5; v/v) as the eluent to give the expected product after crystallization from a DCM/iso ether mixture. m=3.2 g. M.p.=210° C.

Workup

  1. filtrationThe mixture is filtered on C elite
  2. customthe filtrate is evaporated under vacuum
  3. customThe residue is chromatographed on silica using a DCM/AcOEt mixture (95/5; v/v) as the eluent

Sources & evidence

ORD record
ord-f77c3a10b429454292e4300a43247596
Source dataset
uspto-grants-1997_01
Patent number
US05594023

Reaction notes

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