1,2-Dichloroethane → 1-[(6-Bromopyridin-2-yl)methyl]-N-methyl-1H-1,2,3-triazole-4-carboxamide

HRID 2060606Notes

Reaction equation

HRID 2060606 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[CH:13]=[C:12]([C:14]([O-:16])=O)[N:11]=[N:10]2)[CH:5]=[CH:4][CH:3]=1.[K+].C1C=CC2N(O)N=[N:24][C:22]=2C=1.C(Cl)CCl.CN.Cl.CCN(C(C)C)C(C)C>CN(C=O)C.O>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[CH:13]=[C:12]([C:14]([NH:24][CH3:22])=[O:16])[N:11]=[N:10]2)[CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 111,2-Dichloroethane2×HCID 757711-Hydroxybenzotriazole2×HCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochloride2×HCID 86655085Potassium 1-[(6-bromopyridin-2-yl)methyl]-1,2,3-triazole-4-carboxylate

Product 1

HCID 583352651-[(6-Bromopyridin-2-yl)methyl]-N-methyl-1H-1,2,3-triazole-4-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Potassium 1-[(6-bromopyridin-2-yl)methyl]-1,2,3-triazole-4-carboxylate (450 mg, 1.40 mmol), HOBT (429 mg, 2.80 mmol), EDC (537 mg, 2.80 mmol), MeNH2.HCl (284 mg, 4.20 mmol), and DIEA (734 μL, 4.20 mmol) were combined in DMF (5.0 mL) and stirred at room temperature for 2 h. Additional HOBT (429 mg, 2.80 mmol), EDC (537 mg, 2.80 mmol), and MeNH2.HCl (284 mg, 4.20 mmol) were added to push the reaction to completion. After another 2 h at room temperature, the solution was diluted with water and extracted with 5:1 CH2Cl2:MeOH (3×). The combined organic layers were washed with brine, dried (MgSO4), and evaporated. Flash chromatography (0-10% MeOH/CH2Cl2) afforded the title compound as a colorless solid. LRMS (APCI) calc'd for C10H11BrN5O [M+H]+: 296, Found: 296.

Workup

  1. customthe reaction to completion
  2. waitAfter another 2 h at room temperature
  3. extractionextracted with 5:1 CH2Cl2
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated

Sources & evidence

ORD record
ord-76337240ce7744e68a6e01d612c2c598
Source dataset
uspto-grants-2012_10
Patent number
US08278335B2

Reaction notes

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