Sodium Hydroxide → 3-[4-(6-amino-pyridin-3-yl)-[1,2,3]triazol-1-yl]-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide

HRID 1350671Notes

Reaction equation

HRID 1350671 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([CH:27]=[CH:28][C:29]=1[CH3:30])[C:7]([NH:9][C:10]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[C:12]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[C:11]=1[O:25][CH3:26])=[O:8])=[N+:2]=[N-:3].[OH-].[Na+].O=[C:34]1O[C@H]([C@H](CO)O)C([O-])=[C:35]1O.[Na+].[NH2:46][C:47]1[CH:52]=[C:51](C#C)[CH:50]=[CH:49][N:48]=1>CCO.O.CC(O)=O.[O-]S([O-])(=O)=O.[Cu+2]>[NH2:46][C:47]1[N:48]=[CH:49][C:50]([C:34]2[N:3]=[N:2][N:1]([C:4]3[CH:5]=[C:6]([CH:27]=[CH:28][C:29]=3[CH3:30])[C:7]([NH:9][C:10]3[CH:15]=[C:14]([C:16]([CH3:18])([CH3:19])[CH3:17])[CH:13]=[C:12]([NH:20][S:21]([CH3:24])(=[O:22])=[O:23])[C:11]=3[O:25][CH3:26])=[O:8])[CH:35]=2)=[CH:51][CH:52]=1

Participants

9

Reactant 4

HCID 14798Sodium HydroxideHCID 210792023-azido-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamideHCID 210972624-Ethynylpyridin-2-amineHCID 23667548Sodium Ascorbate

Product 1

HCID 210970953-[4-(6-amino-pyridin-3-yl)-[1,2,3]triazol-1-yl]-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide

Reagents, catalysts & solvents 4

HCID 24462Copper SulfateCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent2×HCID 962WaterSolvent3×

Procedure

To a stirring suspension of 310 mg (0.719 mmol) of 3-azido-N-(5-tert-butyl-3-methanesulfonylamino-2-methoxy-phenyl)-4-methyl-benzamide in 2 mL of EtOH and 2 mL of water was added dropwise 4M NaOH until the mixture became homogeneous. A solution of 142 mg (0.719 mmol) of sodium ascorbate in 0.5 mL of water was added, followed by 100 mg (0.719 mmol) 2-amino-4-ethynyl pyridine in 1 mL of EtOH. Finally 0.72 mL of 0.1 M CuSO4 was added, and the resulting mixture was stirred vigorously for 14 h. The mixture was then diluted with 40 mL of water and HOAc was added until a precipitate formed and the pH was about 6. The precipitate was filtered and washed with water and hexanes. The solids were chromatographed (0–5% MeOH/0.5% NH4OH in CH2Cl2) to provide 321 mg (0.584 mmol; 81%) of the title compound. ESI MS m/z 548 [C27H31N7O4S—H]−.

Workup

  1. additionwas added until a precipitate
  2. customformed
  3. filtrationThe precipitate was filtered
  4. washwashed with water and hexanes
  5. customThe solids were chromatographed (0–5% MeOH/0.5% NH4OH in CH2Cl2)

Sources & evidence

ORD record
ord-246e4116f8f04fe1b9ac71c333f655a8
Source dataset
uspto-grants-2007_05
Patent number
US07214802B2

Reaction notes

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