2-Pyridinemethanamine → HCID 23642250, compound

HRID 1520406Notes

Reaction equation

HRID 1520406 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:25]([F:28])([F:27])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([S:20](Cl)(=[O:22])=[O:21])=[C:16]([CH3:24])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:25]([F:28])([F:27])[F:26])[O:13][N:12]=[C:11]([C:14]3[CH:19]=[CH:18][C:17]([S:20]([NH:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=4)(=[O:22])=[O:21])=[C:16]([CH3:24])[CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 195092-PyridinemethanamineHCID 86630501HCID 86630501, compound2×

Product 1

HCID 23642250HCID 23642250, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methylbenzenesulfonyl chloride (i.e. the product of Step B) (0.2 g, 0.42 mmol) in acetonitrile (20 mL) was added 2-(aminomethyl)pyridine (0.108 mL, 1.05 mmol). The reaction mixture was heated to reflux, and then allowed to stir at ambient temperature for 0.5 h. The mixture was then concentrated to dryness and the crude product was purified by silica gel chromatography using hexane:ethyl acetate (80:20) as eluent. The isolated product was triturated with a mixture of ether and hexane to afford the title product, a compound of the present invention, as a white solid (59 mg), m.p. 57-58° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. concentrationThe mixture was then concentrated to dryness
  4. customthe crude product was purified by silica gel chromatography
  5. customThe isolated product was triturated with a mixture of ether and hexane

Sources & evidence

ORD record
ord-7dff555d3bd041069d2363d1c75789f7
Source dataset
uspto-grants-2015_07
Patent number
US09073910B2

Reaction notes

Loading…