Dimethylformamide → HCID 59302969, compound

HRID 1692142Notes

Reaction equation

HRID 1692142 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[C:19](F)[C:18](Cl)=[CH:17][C:16]=2[C:23]2[N:27]([CH3:28])[C:26]([CH2:29][CH3:30])=[N:25][N:24]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:31]([Cu])#[N:32].CN(C=O)C>CCOC(C)=O>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18]([C:31]#[N:32])=[CH:17][C:16]=2[C:23]2[N:27]([CH3:28])[C:26]([CH2:29][CH3:30])=[N:25][N:24]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24996716HCID 24996716, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 59302969HCID 59302969, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A 4 mL scintillation vial was charged with 4-tert-butyl-N-[4-iodo-2-(5-ethyl-4-methyl-4H-[1,2,4]triazol-3-yl)-phenyl]-benzenesulfonamide (prepared according to general procedure C, 18 mg, 0.034 mmol), CuCN (15 mg, 0.17 mmol), and DMF (500 μL). The reaction was then heated to 100° C. and stirred for 48 hours. The solution was then diluted with EtOAc and washed with an aqueous solution of EDTA (5% wt/wt). The organic layer was then concentrated and the residue purified by preparative TLC to afford 4-tert-butyl-N-[4-cyano-2-(5-ethyl-4-methyl-4H-[1,2,4]triazol-3-yl)-phenyl]-benzenesulfonamide as a white solid: MS (ES) M+H expected 424.2, found 424.4.

Workup

  1. washwashed with an aqueous solution of EDTA (5% wt/wt)
  2. concentrationThe organic layer was then concentrated
  3. customthe residue purified by preparative TLC

Sources & evidence

ORD record
ord-bc5453afd321446888784527edcce43f
Source dataset
uspto-grants-2012_04
Patent number
US08153818B2

Reaction notes

Loading…