Triethylamine → 3-(3-(2-Chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-4-methyl-N-(1-methyl-1H-pyrazol-5-yl)benzamide

HRID 643673Notes

Reaction equation

HRID 643673 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]2[CH:13]=[CH:14][C:15]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=3[CH3:26])[C:20]([OH:22])=O)=[CH:16][C:11]2=[N:10][N:9]=1.S(Cl)(Cl)=O.[CH3:31][N:32]1[C:36]([NH2:37])=[CH:35][CH:34]=[N:33]1.C(N(CC)CC)C>C([O-])([O-])=O.[Na+].[Na+]>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]2[CH:13]=[CH:14][C:15]([C:17]3[CH:18]=[C:19]([CH:23]=[CH:24][C:25]=3[CH3:26])[C:20]([NH:37][C:36]3[N:32]([CH3:31])[N:33]=[CH:34][CH:35]=3)=[O:22])=[CH:16][C:11]2=[N:10][N:9]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 1369272-Methyl-2H-pyrazol-3-ylamineHCID 592613633-(3-(2-Chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-4-methylbenzoic acid

Product 1

HCID 592613833-(3-(2-Chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-4-methyl-N-(1-methyl-1H-pyrazol-5-yl)benzamide

Reagents, catalysts & solvents 1

HCID 10340Sodium CarbonateSolvent

Conditions

Temperature
95 °C

Procedure

A mixture of 3-(3-(2-chlorophenyl)-[1,2,4]triazolo[4,3-a]pyridin-7-yl)-4-methylbenzoic acid (2.44 g, 6.7 mmol) and thionyl chloride (30 ml, 411 mmol, Aldrich) was heated to 95° C. for 2 h. The volatiles were removed in vacuo. The solids were re-dissolved in CH2Cl2 (30 ml). A 10 ml aliquot of this solution (860 mg, 2.2 mmol) was treated with 1-methyl-1H-pyrazol-5-amine (656 mg, 6.7 mmol, Maybridge), followed by triethylamine (939 μl, 6.7 mmol, Aldrich). The mixture was diluted with 10% Na2CO3 and extracted with CH2Cl2 (3×). The combined organics were dried over Na2SO4, filtered and concentrated over silica gel. The residue was purified using column chromatography (Acetone/Hexanes=0-50%). The mixture was dissolved in MeOH and loaded onto an Agilent AccuBOND II SCX solid phase extraction column. After washing with MeOH, the title compound was eluted with 2M NH3 in MeOH. The residue was recrystallized from MeOH yielding the title compound as a white solid. HRMS (TOF) Calcd for C24H20ClN6O+: 443.1382, found: 443.1389.

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionThe solids were re-dissolved in CH2Cl2 (30 ml)
  3. extractionextracted with CH2Cl2 (3×)
  4. dry with materialThe combined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated over silica gel
  7. customThe residue was purified
  8. dissolutionThe mixture was dissolved in MeOH
  9. extractionloaded onto an Agilent AccuBOND II SCX solid phase extraction column
  10. washAfter washing with MeOH
  11. washthe title compound was eluted with 2M NH3 in MeOH
  12. customThe residue was recrystallized from MeOH yielding the title compound as a white solid

Sources & evidence

ORD record
ord-f29ac0ac7ed34200b929b3f26af07751
Source dataset
uspto-grants-2010_04
Patent number
US07700593B2

Reaction notes

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