Sodium Hydroxide → 3-{4-[6-(Cyclopropylmethyl-amino)-pyridin-3-yl]-1,2,3-triazol-1-yl}-4-methyl-benzoic acid

HRID 2109149Notes

Reaction equation

HRID 2109149 reaction equation
[N:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:7]([OH:9])=[O:8])=[N+:2]=[N-:3].[OH-].[Na+].[CH:16]1([CH2:19][NH:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]#[CH:28])=[CH:23][N:22]=2)[CH2:18][CH2:17]1.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+].[NH4+].[OH-]>CCO.O.CO.[O-]S([O-])(=O)=O.[Cu+2].CC(O)=O>[CH:16]1([CH2:19][NH:20][C:21]2[N:22]=[CH:23][C:24]([C:27]3[N:3]=[N:2][N:1]([C:4]4[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=4[CH3:13])[C:7]([OH:9])=[O:8])[CH:28]=3)=[CH:25][CH:26]=2)[CH2:17][CH2:18]1

Participants

11

Reactant 5

HCID 14798Sodium HydroxideHCID 14923Ammonium HydroxideHCID 179730913-Azido-4-methylbenzoic acidHCID 210972782-(Cyclopropylmethyl)amino-5-ethynyl pyridineHCID 23667548Sodium Ascorbate

Product 1

HCID 210972943-{4-[6-(Cyclopropylmethyl-amino)-pyridin-3-yl]-1,2,3-triazol-1-yl}-4-methyl-benzoic acidYield 66.7%

Reagents, catalysts & solvents 5

HCID 24462Copper SulfateCatalystHCID 176Acetic AcidSolvent2×HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent3×

Procedure

3-Azido-4-methyl benzoic acid (497 mg; 2.81 mmol) was suspended in 6.5 mL of EtOH. To this mixture was added 4N NaOH until the mixture became homogeneous, followed then by 2-(cyclopropylmethyl)amino-5-ethynyl pyridine (460 mg; 2.61 mmol) and 529 mg (2.67 mmol) of sodium ascorbate in 0.7 mL of water. The mixture was stirred rapidly as 2.67 mL of a 0.1 M CuSO4 solution was added. A yellow precipitate formed and the mixture was stirred rapidly for 14 h. The mixture was poured into water and acidified carefullly with HOAc. The resulting precipitate was filtered and washed with water. A fine yellow powder was isolated. This material was crushed in 1 mL of MeOH and 5 mL of NH4OH was added. The resulting green mixture was stirred for 10 min, then HOAc was carefully added until a white precipitate formed (pH 8-9). The precipitate was filtered and washed with 1% HOAc in water, then with water and hexanes to provide 607 mg (1.74 mmol; 65%) of 3-{4-[6-(cyclopropylmethyl-amino)-pyridin-3-yl]-1,2,3-triazol-1-yl}-4-methyl-benzoic acid.

Workup

  1. additionwas added
  2. customA yellow precipitate formed
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with water
  5. customA fine yellow powder was isolated
  6. stirringThe resulting green mixture was stirred for 10 min
  7. customformed (pH 8-9)
  8. filtrationThe precipitate was filtered
  9. washwashed with 1% HOAc in water

Sources & evidence

ORD record
ord-cfa846ff348e40538205862b405e89ac
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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