Diisopropylethylamine → HCID 86688146, compound

HRID 1622571Notes

Reaction equation

[N:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6](C(O)=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.CC[N:16]([CH:20](C)C)C(C)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:30])=CC=1.Cl.[F:41][C:42]([F:62])([F:61])[C:43]1[CH:48]=[CH:47][C:46]([C@@H:49]([C:51]2[C:56]([C:57]([F:60])([F:59])[F:58])=[CH:55][CH:54]=[CH:53][N:52]=2)[NH2:50])=[CH:45][CH:44]=1>O1CCOCC1>[N:1]1[C:10]2[C:5](=[C:6]([NH:16][C:20]([NH:50][C@@H:49]([C:46]3[CH:45]=[CH:44][C:43]([C:42]([F:61])([F:41])[F:62])=[CH:48][CH:47]=3)[C:51]3[C:56]([C:57]([F:60])([F:58])[F:59])=[CH:55][CH:54]=[CH:53][N:52]=3)=[O:30])[CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of quinoline-5-carboxylic acid (0.054 g, 0.312 mmol), DIPEA (0.054 mL, 0.312 mmol), and DPPA (0.067 mL, 0.312 mmol) in 1,4-dioxane (2 mL) was stirred at rt for 1 h. (S)-(4-(Trifluoromethyl)phenyl)(3-(trifluoromethyl)pyridin-2-yl)methanamine hydrochloride (Intermediate 1) (0.100 g, 0.312 mmol) was added, and the resulting mixture was heated at 85° C. for 24 h. The reaction mixture was cooled, concentrated, and purified by ISCO (Silica gel, 0-75% EtOAc/hexanes) to give the title compound. 1H-NMR (300 MHz, MeOH-d4): δ ppm 8.93 (d, J=4.5 Hz, 1H), 8.82 (d, J=3.5 Hz, 1H), 8.46 (d, J=8.5 Hz, 1H), 8.18 (d, J=8.0 Hz, 1H), 7.85 (d, J=7.3 Hz, 1H), 7.75-7.83 (m, 1H), 7.71 (d, J=7.7 Hz, 1H), 7.54-7.68 (m, 5H), 7.51 (dd, J=8.6, 4.2 Hz, 1H), 6.67 (s, 1H). MS (ESI pos. ion) m/z: 491.0 (M+H).

Workup

additionwas added
temperatureThe reaction mixture was cooled
concentrationconcentrated
custompurified by ISCO (Silica gel, 0-75% EtOAc/hexanes)

Sources & evidence

ORD record: ord-f3b5c35f69af491fa8c9933d9d6aa87d
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08778941B2

Reaction notes

Loading…