Dimethylformamide → 3-[2-acetoxy-4-methylthiobenzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide

HRID 1434845Notes

Reaction equation

HRID 1434845 reaction equation
[C:1]([O:4][C:5]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:6]=1[C:7](O)=[S:8])(=[O:3])[CH3:2].CCN(CC)CC.CN(C=O)C.C(Cl)(=O)C(Cl)=O.[NH2:33][C:34]1[C:35]([C:40]([NH:42][C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][N:44]=2)=[O:41])=[N:36][CH:37]=[CH:38][CH:39]=1>ClCCl>[C:1]([O:4][C:5]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:6]=1[C:7]([NH:33][C:34]1[C:35]([C:40]([NH:42][C:43]2[CH:48]=[CH:47][C:46]([Cl:49])=[CH:45][N:44]=2)=[O:41])=[N:36][CH:37]=[CH:38][CH:39]=1)=[S:8])(=[O:3])[CH3:2]

Participants

7

Reactant 5

HCID 6228DimethylformamideHCID 8471Triethylamine2×HCID 65578Oxalyl chlorideHCID 115578513-amino-N-(5-chloropyridin-2-yl)pyridine-2-carboxamideHCID 178475392HCID 178475392, compound

Product 1

HCID 866200023-[2-acetoxy-4-methylthiobenzoylamino]-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. mixture of 2-acetoxy-4-methylthiobenzoic acid (5 g, 22.1 mmol), dichloromethane (75 mL), NEt3 (3.1 mL, 22.1 mmol) and DMF (17 μL, 0.221 mmol) was added oxalyl chloride (1.92 mL, 22.1 mL) at a rate to give gentle bubbling. The mixture was stirred for 1 h and then was concentrated in vacuo. The resulting residue was dissolved in dichloromethane (75 mL). To this solution was added 3-amino-N-(5-chloropyridin-2-yl)pyridine-2-carboxamide (5.5 g, 22.1 mmol) followed by NEt3 (3.1 mL, 22.1 mmol). The reaction mixture was stirred for 18 h, concentrated to a slurry in dichloromethane and chromatographed (75 g silica gel; 100% dichloromethane to 100% EtOAc) to give the title compound as an impure solid (8.5 g).

Workup

  1. customto give gentle bubbling
  2. concentrationwas concentrated in vacuo
  3. dissolutionThe resulting residue was dissolved in dichloromethane (75 mL)
  4. stirringThe reaction mixture was stirred for 18 h
  5. concentrationconcentrated to a slurry in dichloromethane
  6. customchromatographed (75 g silica gel; 100% dichloromethane to 100% EtOAc)

Sources & evidence

ORD record
ord-45f5d4e6a6c343d9960f40ccc9d66f68
Source dataset
uspto-grants-2009_11
Patent number
US07615568B2

Reaction notes

Loading…