Triethylamine → HCID 57893665, compound

HRID 1822055Notes

Reaction equation

[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[N:4]=1.C(N(CC)CC)C.[F:24][C:25]1[CH:33]=[C:32]([F:34])[CH:31]=[C:30]([F:35])[C:26]=1[C:27](Cl)=[O:28]>C1COCC1>[F:24][C:25]1[CH:33]=[C:32]([F:34])[CH:31]=[C:30]([F:35])[C:26]=1[C:27]([N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)[N:4]=1)=[O:28]

Participants

Conditions

Temperature: 55 °C

Procedure

Dissolve the above amine product in THF (6 mL), add triethylamine (219 mg, 0.29 mL, 2.08 mmol) and 2,4,6-trifluorobenzoyl chloride (303 mg, 1.56 mmol) sequentially, heat at 55° C. overnight. Quench with 0.1N NaOH, extract with methylene dichloride three times. Combine the organic layers, dry over Na2SO4, filter and concentrate to give a residue. Chromatography (silica gel) eluting with 3.5% 2M NH3-methanol in methylene dichloride provides 204 mg (43% two-step yield) of the title compound as a colorless oil: mass spectrum (ion spray): m/z=380.1 (M+1); 1H NMR (CDCl3, ppm): 7.47 (t, 1H), 6.53 (m, 4H), 4.74 (m, 1H), 3.48 (s, 3H), 2.71 (m, 2H), 2.32 (s, 3H), 2.25 (m, 2H), 1.91 (m, 2H), 1.72 (m, 2H). Mono-hydrochloride salt: Anal. calc for C19H20F3N3O2.HCl.0.5H2O: C, 53.72; H, 5.22; N, 9.89. Found: C, 53.84; H, 5.04; N, 9.73.

Workup

customQuench with 0.1N NaOH
extractionextract with methylene dichloride three times
dry with materialCombine the organic layers, dry over Na2SO4
filtrationfilter
concentrationconcentrate
customto give a residue
washChromatography (silica gel) eluting with 3.5% 2M NH3-methanol in methylene dichloride
customprovides

Sources & evidence

ORD record: ord-d450e73fa4eb42eda6ed1376f2e8803d
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608629B2

Reaction notes

Loading…