Triethylamine → HCID 24963706, compound

HRID 1666367Notes

Reaction equation

[Br:1][C:2]1[N:7]=[CH:6][C:5]([NH:8][C:9](=O)[O:10]C2C=CC=CC=2)=[CH:4][CH:3]=1.[NH:18]1[CH2:23][CH2:22][C:21](=[CH:24][C:25]2[CH:26]=[C:27]([CH:39]=[CH:40][CH:41]=2)[O:28][C:29]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][N:30]=2)[CH2:20][CH2:19]1.C(N(CC)CC)C>CS(C)=O>[F:37][C:35]([F:38])([F:36])[C:32]1[CH:33]=[CH:34][C:29]([O:28][C:27]2[CH:26]=[C:25]([CH:41]=[CH:40][CH:39]=2)[CH:24]=[C:21]2[CH2:22][CH2:23][N:18]([C:9]([NH:8][C:5]3[CH:6]=[N:7][C:2]([Br:1])=[CH:3][CH:4]=3)=[O:10])[CH2:19][CH2:20]2)=[N:30][CH:31]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of phenyl 6-bromopyridin-3-ylcarbamate (1.03 g, 3.5 mmol) in DMSO (5 mL) was added 2-(3-(piperidin-4-ylidenemethyl)phenoxy)-5-(trifluoromethyl)pyridine (1.3 g, 3.51 mmol) followed by triethylamine (0.98 mL, 7.01 mmol). The reaction was stirred at 60° C. overnight and then allowed to cool to RT. The reaction mixture was partitioned between EtOAc and water. The organic layer was washed with brine, dried over MgSO4 and concentrated. Purification by silica gel column chromatography (0-5% MeOH/CH2Cl2) afforded the title compound as an oil, which foamed up on the pump (1.76 g, 94% yield). MS (APCI 10V) AP+2 535.08; 1H NMR (400 MHz, CDCl3) δ ppm 2.46 (t, 2H) 2.59 (t, 2H) 3.50 (t, 2H) 3.59 (t, 2H) 6.40 (s, 1H) 6.47 (br. s., 1H) 6.97-7.03 (m, 3H) 7.08 (d, 1H) 7.36-7.41 (m, 2H) 7.87-7.92 (m, 2H) 8.20 (d, 1H) 8.43 (d, 1H).

Workup

temperatureto cool to RT
customThe reaction mixture was partitioned between EtOAc and water
washThe organic layer was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated
customPurification by silica gel column chromatography (0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-91fe42a31f9a4186af809a5425971d4f
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044052B2

Reaction notes

Loading…