(Diethylamino)sulfur trifluoride → HCID 86297690, compound

HRID 594073Notes

Reaction equation

[F:1][CH:2](F)[C:3]1[CH:21]=[CH:20][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[O:8])=[CH:5][C:4]=1[C:22]1[CH:27]=[CH:26][N:25]=[C:24]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)[CH:23]=1.C(N(S(F)(F)F)CC)C>C(Cl)Cl>[F:1][CH2:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[CH:11]=2)=[O:8])=[CH:5][C:4]=1[C:22]1[CH:27]=[CH:26][N:25]=[C:24]([N:28]2[CH2:29][CH2:30][O:31][CH2:32][CH2:33]2)[CH:23]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a cooled solution of 4-(difluoromethyl)-3-(2-morpholinopyridin-4-yl)-N-(3-(trifluoromethyl)phenyl)benzamide (1.0 equiv.) in dry CH2Cl2 (0.05 M), (diethylamino)sulfur trifluoride (3.5 equiv.) was added portionwise under vigorous stirring. The resulting reaction mixture was stirred at −78° C. for 3 hrs, Quenched the reaction with sat NaHCO3 and extracted with DCM. The organic layer was washed with Brine, filtered over Na2SO4 and concentrated. The residue was purified by PREP HPLC to yield 4-(fluoromethyl)-3-(2-morpholinopyridin-4-yl)-N-(3-(trifluoromethyl)phenyl)benzamide in 16% yield. 1H NMR (400 MHz, <cd3od>) δ ppm 3.68 (d, J=5.09 Hz, 4H), 3.86 (d, J=5.09 Hz, 4H), 5.40 (s, 1H), 5.52 (s, 1H), 7.01-7.11 (m, 1H), 7.24-7.31 (m, 1H), 7.41-7.48 (m, 1H), 7.52-7.60 (m, 1H), 7.77-7.83 (m, 1H), 7.91-7.98 (m, 1H), 7.99-8.04 (m, 1H), 8.07-8.19 (m, 3H). LC/MS (m/z)=460.1 (MH+), R=0.85 min.

Workup

customThe resulting reaction mixture
customQuenched
customthe reaction with sat NaHCO3
extractionextracted with DCM
washThe organic layer was washed with Brine
filtrationfiltered over Na2SO4
concentrationconcentrated
customThe residue was purified by PREP HPLC

Sources & evidence

ORD record: ord-0e027f36c1184da49b259f212fa0bb46
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09242969B2

Reaction notes

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