Pyridine → 4-tert-butyl-N-[4-chloro-5-fluoro-2-(4-methyl-5-oxazol-4-yl-4H-[1,2,4]triazol-3-yl)-phenyl]-benzenesulfonamide

HRID 1692126Notes

Reaction equation

HRID 1692126 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[N:6]=[CH:7][O:8][CH:9]=1)=O.O=P(Cl)(Cl)Cl.N1C=CC=CC=1.[C:21]([C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH:34][C:35]2[CH:40]=[C:39]([F:41])[C:38]([Cl:42])=[CH:37][C:36]=2[C:43]([NH:45][NH2:46])=O)(=[O:33])=[O:32])=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22].C(NC(C)C)(C)C>O1CCOCC1.CC#N>[C:21]([C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH:34][C:35]2[CH:40]=[C:39]([F:41])[C:38]([Cl:42])=[CH:37][C:36]=2[C:43]2[N:2]([CH3:1])[C:3]([C:5]3[N:6]=[CH:7][O:8][CH:9]=3)=[N:46][N:45]=2)(=[O:33])=[O:32])=[CH:27][CH:26]=1)([CH3:23])([CH3:24])[CH3:22]

Participants

8

Reactant 5

HCID 1049PyridineHCID 7912DiisopropylamineHCID 24813Phosphorus oxychlorideHCID 17866874N-Methyl-4-oxazolecarboxamideHCID 593029664-tert-butyl-N-(4-chloro-5-fluoro-2-hydrazinocarbonyl-phenyl)-benzenesulfonamide

Product 1

HCID 249922524-tert-butyl-N-[4-chloro-5-fluoro-2-(4-methyl-5-oxazol-4-yl-4H-[1,2,4]triazol-3-yl)-phenyl]-benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

A 25 mL scintillation vial was charged with oxazole-4-carboxylic acid methylamide (132 mg, 1.0 mmol), POCl3 (0.27 mL, 3 mmol), pyridine (0.48 mL, 6 mmol) 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-(4-chloro-5-fluoro-2-hydrazinocarbonyl-phenyl)-benzenesulfonamide (400 mg, 1.0 mmol), diisopropylamine (2.0 mL), and dioxane (2.0 mL). The vial was sealed, heated to 130° C., and stirred for two hours. The volatiles were then removed in vacuo, and the residue was purified via automated silica gel chromatography and then HPLC to afford 4-tert-butyl-N-[4-chloro-5-fluoro-2-(4-methyl-5-oxazol-4-yl-4H-[1,2,4]triazol-3-yl)-phenyl]-benzenesulfonamide as a white powder: 1H NMR (400 MHz, CDCl3) δ 9.72 (s, 1H), 8.48 (d, 1H), 8.04 (d, 1H), 7.67 (d, 1H), 7.50 (d, 2H), 7.33 (d, 1H), 7.3 (d, 2H), 3.59 (s, 3H), 1.23 (s, 9H), MS (ES) M+H expected 490.1, found 490.0.

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 were then removed in vacuo
  7. customthe residue was purified

Sources & evidence

ORD record
ord-3e6c12376cb14e0ba5c514bd6922cf01
Source dataset
uspto-grants-2012_04
Patent number
US08153818B2

Reaction notes

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