benzyl 6-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-ylcarbamate → 6-(4-Cyclopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-amine

HRID 2178590Notes

Reaction equation

HRID 2178590 reaction equation
[CH:1]1([N:4]2[CH:8]=[N:7][N:6]=[C:5]2[C:9]2[N:14]=[C:13]([NH:15]C(=O)OCC3C=CC=CC=3)[CH:12]=[CH:11][CH:10]=2)[CH2:3][CH2:2]1>[Pd]>[CH:1]1([N:4]2[CH:8]=[N:7][N:6]=[C:5]2[C:9]2[N:14]=[C:13]([NH2:15])[CH:12]=[CH:11][CH:10]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 66851549benzyl 6-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-ylcarbamate

Product 1

HCID 581029666-(4-Cyclopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-amineYield 100.2%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A mixture of benzyl 6-(4-cyclopropyl-4H-1,2,4-triazol-3-yl)pyridin-2-ylcarbamate (660 mg, 1.96 mmol, 1.0 eq) and Pd/C (80 mg 10% Pd loading, 40 mg/mmol) was loaded into a flask and purged with nitrogen. Ethanol (0.4 M) was added and the flask was charged with hydrogen (1 atm—balloon pressure). The reaction was stirred at room temperature for 90 minutes, and judged to be complete by TLC. The reaction mixture was filtered through celite, and concentrated under reduced pressure to give 395 mg (95%) of 6-(4-cyclopropyl-4H-[1,2,4]triazol-3-yl)-pyridin-2-ylamine. C10H11N5. 202.1 (M+1). 1H NMR (DMSO) d 8.14 (s, 1H), 7.54 (t, J=8 Hz, 1H), 7.46 (d, J=7 Hz, 1H), 6.60 (d, J=8 Hz, 1H), 4.70 (br s, 2H), 3.85-3.88 (m, 1H), 1.04-1.07 (m, 2H), 0.85-0.88 (m, 2H).

Workup

  1. customwas loaded into a flask
  2. custompurged with nitrogen
  3. additionEthanol (0.4 M) was added
  4. additionthe flask was charged with hydrogen (1 atm—balloon pressure)
  5. filtrationThe reaction mixture was filtered through celite
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4c28c5ffa24e48cdbb95fd587b508064
Source dataset
uspto-grants-2015_06
Patent number
US09067933B2

Reaction notes

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