Triethylamine → [8-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-methoxy-phenyl)-amine

HRID 472290Notes

Reaction equation

HRID 472290 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[N:24]=[C:13]3[C:14]([C:18]4[CH2:19][CH2:20][NH:21][CH2:22][CH:23]=4)=[CH:15][CH:16]=[CH:17][N:12]3[N:11]=2)=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>ClCCl.O>[CH3:32][S:33]([N:21]1[CH2:20][CH:19]=[C:18]([C:14]2[C:13]3[N:12]([N:11]=[C:10]([NH:9][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=4)[N:24]=3)[CH:17]=[CH:16][CH:15]=2)[CH2:23][CH2:22]1)(=[O:35])=[O:34]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67481385(4-Methoxy-phenyl)-[8-(1,2,3,6-tetrahydro-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amine

Product 1

HCID 67479063[8-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-methoxy-phenyl)-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (4-methoxy-phenyl)-[8-(1,2,3,6-tetrahydro-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-amine (47.0 mg, 0.146 mmol) and triethylamine (31.0 uL, 0.222 mmol) in dichloromethane (2 mL) was added dropwise methanesulfonyl chloride (14.0 L, 0.181 mmol). The mixture was stirred at room temperature for 1 hour then diluted with dichloromethane (20 mL) and water (20 mL). The organic was washed with water and saturated aqueous sodium bicarbonate (10 mL), dried over magnesium sulfate, filtered and evaporated. The residue was purfied via chromatography using amine modified silica gel column (4.7 g) using 5%→100% ethyl acetate:hexane solvent gradient. The title compound, [8-(1-Methanesulfonyl-1,2,3,6-tetrahydro-pyridin-4-yl)-[1,2,4]triazolo[1,5-a]pyridin-2-yl]-(4-methoxy-phenyl)-amine, was isolated as a yellow solid (0.037 g, 63%). MP=194-198° C. 1H NMR (400 MHz, CDCl3, δ, ppm): 8.33 (dd, J=6.6, 0.9 Hz, 1H), 7.52-7.47 (m, 2H), 7.32 (dd, J=7.5, 0.8 Hz, 1H), 7.29-7.25 (m, 1H), 6.94-6.89 (m, 2H), 6.86 (dd, J=7.5, 6.8 Hz, 1H), 6.73 (s, 1H), 4.10-4.06 (m, 2H), 3.81 (s, 3H), 3.57 (t, J=5.7 Hz, 2H), 2.87 (s, 3H), 2.84-2.78 (m, 2H). MS=400 (MH)+.

Workup

  1. washThe organic was washed with water and saturated aqueous sodium bicarbonate (10 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-5b7a83eaa084402f81b0b8d5fe367762
Source dataset
uspto-grants-2014_01
Patent number
US08633173B2

Reaction notes

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