2,6-Lutidine → 4-tert-butyl-N-[6-chloro-2-(4-isopropyl-5-methoxymethyl-4H-[1,2,4]triazol-3-yl)-pyridin-3-yl]-benzenesulfonamide

HRID 2094211Notes

Reaction equation

HRID 2094211 reaction equation
[CH:1]([NH:4][C:5](=O)[CH2:6][O:7][CH3:8])([CH3:3])[CH3:2].O=P(Cl)(Cl)Cl.N1C(C)=CC=CC=1C.[C:23]([C:27]1[CH:32]=[CH:31][C:30]([S:33]([NH:36][C:37]2[C:38]([C:44]([NH:46][NH2:47])=O)=[N:39][C:40]([Cl:43])=[CH:41][CH:42]=2)(=[O:35])=[O:34])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24].CCN(C(C)C)C(C)C>O1CCOCC1.CC#N>[C:23]([C:27]1[CH:28]=[CH:29][C:30]([S:33]([NH:36][C:37]2[C:38]([C:44]3[N:4]([CH:1]([CH3:3])[CH3:2])[C:5]([CH2:6][O:7][CH3:8])=[N:47][N:46]=3)=[N:39][C:40]([Cl:43])=[CH:41][CH:42]=2)(=[O:34])=[O:35])=[CH:31][CH:32]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

8

Reactant 5

HCID 79372,6-LutidineHCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 193536202-Methoxy-N-(propan-2-yl)acetamideHCID 866183534-tert-butyl-N-(6-chloro-2-hydrazinocarbonyl-pyridin-3-yl)-benzenesulfonamide

Product 1

HCID 866183544-tert-butyl-N-[6-chloro-2-(4-isopropyl-5-methoxymethyl-4H-[1,2,4]triazol-3-yl)-pyridin-3-yl]-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

A 25 mL scintillation vial was charged with N-isopropyl-2-methoxyacetamide (132 mg, 1.0 mmol), POCl3 (0.19 mL, 2.0 mmol), 2,6-lutidine (0.30 mL, 2.4 M), and CH3CN (10 mL). The vial was sealed, heated to 40° C., and stirred for four hours. The volatiles were then evacuated in vacuo and to the residue was added 4-tert-butyl-N-(6-chloro-2-hydrazinocarbonyl-pyridin-3-yl)-benzenesulfonamide (193 mg, 0.5 mmol), DIPEA (2.0 mL), and dioxane (2.0 mL). The vial was sealed, heated to 130° C., and stirred for two hours. The volatiles was then evacuated in vacuo, and the residue was purified via automated silica gel chromatography and then preparative HPLC to afford 4-tert-butyl-N-[6-chloro-2-(4-isopropyl-5-methoxymethyl-4H-[1,2,4]triazol-3-yl)-pyridin-3-yl]-benzenesulfonamide as a white powder: MS (ES) M+H expected 478.2. found 478.1.

Workup

  1. customThe vial was sealed
  2. customThe volatiles were then evacuated in vacuo and to the residue
  3. customThe vial was sealed
  4. temperatureheated to 130° C.
  5. stirringstirred for two hours
  6. customThe volatiles was then evacuated in vacuo
  7. customthe residue was purified

Sources & evidence

ORD record
ord-4926adff082d4e4391418707ee372752
Source dataset
uspto-grants-2013_05
Patent number
US08445518B2

Reaction notes

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