HCID 178418361, compound → HCID 178474074, compound

HRID 2402095Notes

Reaction equation

HRID 2402095 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[C:12]([C:32]#[N:33])=[C:13]([C:21]3[CH:26]=[CH:25][N+:24]([O-])=[C:23]([NH:28][C:29](=[O:31])[CH3:30])[CH:22]=3)[S:14][C:15]=2[C:16]2[NH:20][CH:19]=[N:18][N:17]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H][H]>CO.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[C:12]([C:32]#[N:33])=[C:13]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:28][C:29](=[O:31])[CH3:30])[CH:22]=3)[S:14][C:15]=2[C:16]2[NH:20][CH:19]=[N:18][N:17]=2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178474075HCID 178474075, compound

Product 1

HCID 178474074HCID 178474074, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N-{4-[4-[(4-chlorophenyl)sulfonyl]-3-cyano-5-(4H-1,2,4-triazol-3-yl)-2-thienyl]-1-oxidopyridin-2-yl}acetamide (0.0229 g, 0.0457 mmol) was dissolved in methanol (3.00 mL), followed by the addition of 10% Pd—C (5 mg). The flask was filled with hydrogen at 40 psi, and the suspension was stirred at room temperature for overnight. The solid was filtered off, and the residue was concentrated followed by purification by column chromatography. The eluent was 0-8% methanol in ethyl acetate to yield a solid product (0.0142 g, yield 64.0%). LCMS: (AA) ES+ 485, 487. 1H NMR (300 MHz, MeOD) δ: 8.60 (s, 1H), 8.53 (s, 1H), 8.45 (d, 1H), 8.35 (d, 2H), 7.66 (d, 2H), 7.48 (d, 1H), 2.20 (s, 3H).

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe residue was concentrated
  3. customfollowed by purification by column chromatography

Sources & evidence

ORD record
ord-c8948baaff5e42948e8d5803dd495299
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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