Dimethylamine → HCID 24803942, compound

HRID 2094213Notes

Reaction equation

HRID 2094213 reaction equation
C([O:3][C:4]([C:6]1[N:10]([CH:11]([CH3:13])[CH3:12])[C:9]([C:14]2[C:19]([NH:20][S:21]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([CH3:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=3)(=[O:23])=[O:22])=[CH:18][C:17]([Cl:34])=[CH:16][N:15]=2)=[N:8][N:7]=1)=O)C.[CH3:35][NH:36][CH3:37].[C-]#N.[K+]>C1COCC1>[CH3:35][N:36]([CH3:37])[C:4]([C:6]1[N:10]([CH:11]([CH3:13])[CH3:12])[C:9]([C:14]2[C:19]([NH:20][S:21]([C:24]3[CH:25]=[CH:26][C:27]([C:30]([CH3:31])([CH3:32])[CH3:33])=[CH:28][CH:29]=3)(=[O:23])=[O:22])=[CH:18][C:17]([Cl:34])=[CH:16][N:15]=2)=[N:8][N:7]=1)=[O:3]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 9032Potassium CyanideHCID 24803941HCID 24803941, compound

Product 1

HCID 24803942HCID 24803942, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A 25 mL scintillation vial was charged with 5-[3-(4-tert-butyl-benzenesulfonylamino)-5-chloro-pyridin-2-yl]-4-isopropyl-4H-[1,2,4]triazole-3-carboxylic acid ethyl ester (prepared according to general procedure B, 11 mg, 0.02 mmol), dimethylamine in THF (2 mL, 2.0 M), and KCN (1 mg, 0.01 mmol). The vial was sealed and stirred at 50° C. for 16 h. The volatiles were then evacuated in vacuo and the residue was purified via preparatory HPLC to afford 4-tert-butyl-N-[6-chloro-2-(4-ethyl-5-methyl-4H-[1,2,4]triazol-3-yl)-pyridin-3-yl]-enzenesulfonamide as a white powder: MS (ES) M+H expected 505.2. found 505.5.

Workup

  1. customThe vial was sealed
  2. customThe volatiles were then evacuated in vacuo
  3. customthe residue was purified via preparatory HPLC
  4. customto afford 4-tert-butyl-N-[6-chloro-2-(4-ethyl-5-methyl-4H-[1,2,4]triazol-3-yl)-pyridin-3-yl]-enzenesulfonamide as a white powder

Sources & evidence

ORD record
ord-9e18477e403a4f4b87e6cd45e22add3d
Source dataset
uspto-grants-2013_05
Patent number
US08445518B2

Reaction notes

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