HCID 131732257, compound → HCID 131732258, compound

HRID 1424796Notes

Reaction equation

HRID 1424796 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:11]([C:16]2[C:35]([CH:36]3[CH2:38][CH2:37]3)=[CH:34][C:19]3[C:20]([C:30]([NH:32][CH3:33])=[O:31])=[C:21]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=4)[O:22][C:18]=3[CH:17]=2)[S:12]([CH3:15])(=[O:14])=[O:13])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O>[Pt].CO.C1COCC1>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([N:11]([C:16]2[C:35]([CH:36]3[CH2:38][CH2:37]3)=[CH:34][C:19]3[C:20]([C:30]([NH:32][CH3:33])=[O:31])=[C:21]([C:23]4[CH:24]=[CH:25][C:26]([Cl:29])=[CH:27][CH:28]=4)[O:22][C:18]=3[CH:17]=2)[S:12]([CH3:15])(=[O:14])=[O:13])=[CH:3][C:2]=1[Cl:1]

Participants

4

Reactant 1

HCID 131732257HCID 131732257, compound

Product 1

HCID 131732258HCID 131732258, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 6-(N-(3-chloro-4-nitrophenyl)methylsulfonamido)-2-(4-chlorophenyl)-5-cyclopropyl-N-methylbenzofuran-3-carboxamide (0.500 g, 0.870 mmol) in 3:1 MeOH/THF (30 mL) was subjected to hydrogenation at 45 psi in the presence of 5% sulfided platinum on carbon (50 mg). After 18 hours the reaction vessel was purged with nitrogen, catalyst removed by filtration through celite and the filtrate concentrated to dryness at reduced pressure. The residue was recrystallized from hexane/EtOAc to afford the title compound (0.45 g, 95%) as an off-white solid. LCMS (m/z, ES+)=544 (M+H+).

Workup

  1. customAfter 18 hours the reaction vessel was purged with nitrogen, catalyst
  2. customremoved by filtration through celite
  3. concentrationthe filtrate concentrated to dryness at reduced pressure
  4. customThe residue was recrystallized from hexane/EtOAc

Sources & evidence

ORD record
ord-db73dfb4a466421485bdfa7e50c9e7c7
Source dataset
uspto-grants-2015_01
Patent number
US08927593B2

Reaction notes

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