Dimethylformamide → HCID 59302969, compound

HRID 448120Notes

Reaction equation

HRID 448120 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[CH:20]=[CH:19][C:18](I)=[CH:17][C:16]=2[C:22]2[N:26]([CH3:27])[C:25]([CH2:28][CH3:29])=[N:24][N:23]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:30]([Cu])#[N:31].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:30]#[N:31])=[CH:17][C:16]=2[C:22]2[N:26]([CH3:27])[C:25]([CH2:28][CH3:29])=[N:24][N:23]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 59302965HCID 59302965, 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-0b1f71987726420c84c69c825c938e1c
Source dataset
uspto-grants-2013_07
Patent number
US08481579B2

Reaction notes

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