3-Amino-1-propanol → HCID 59444621, compound

HRID 603477Notes

Reaction equation

HRID 603477 reaction equation
Cl[C:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][C:15]([CH2:18][CH3:19])=[CH:14][CH:13]=2)[N:3]=1.[NH2:20][CH2:21][CH2:22][CH2:23][OH:24]>CC#N.C(O)(C(F)(F)F)=O>[CH2:18]([C:15]1[CH:16]=[CH:17][C:12]([C:4]2[N:3]=[C:2]([NH:20][CH2:21][CH2:22][CH2:23][OH:24])[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:5]=2)=[CH:13][CH:14]=1)[CH3:19]

Participants

5

Reactant 2

HCID 90863-Amino-1-propanolHCID 593004782-Chloro-6-(4-ethylphenyl)-3-(trifluoromethyl)pyridine

Product 1

HCID 59444621HCID 59444621, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 2-chloro-6-(4-ethylphenyl)-3-(trifluoromethyl)pyridine (Example 315, 0.36 g, 1.25 mmol) and 3-amino-1-propanol (0.38 g, 5.00 mmol) in CH3CN (2 mL), TFA (0.5 mL) was added. The mixture was stirred at reflux for 18 h, and then concentrated under reduced pressure. The product (0.21 g, 52%) was isolated after silica gel flash chromatography (2:1 hexanes/EtOAc). 1H NMR (400 MHz, CD3OD) δ 7.95 (d, 2H), 7.72 (d, 1H), 7.27 (d, 2H), 7.10 (d, 1H), 3.72 (t, 2H), 3.66 (t, 2H), 2.69 (q, 2H), 1.90 (q, 2H), 1.27 (t, 3H).

Workup

  1. temperatureat reflux for 18 h
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9a200002c2df4e07b2ab04284d15aa2a
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

Loading…