Water → Methyl 1-{5-[({5-[(3,4-difluorophenyl)amino]-1,3,4-oxadiazol-2-yl}carbonyl)amino]pyridin-2-yl}-4-methylpiperidine-4-carboxylate

HRID 1713779Notes

Reaction equation

[NH:1]([C:3](=[O:24])[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:18][CH2:17][C:16]([CH3:23])([C:19]([O:21][CH3:22])=[O:20])[CH2:15][CH2:14]2)=[N:11][CH:12]=1)=[O:5])[NH2:2].[F:25][C:26]1[CH:27]=[C:28]([N:33]=[C:34]=S)[CH:29]=[CH:30][C:31]=1[F:32].CCN=C=NCCCN(C)C.Cl.O>CN(C=O)C>[F:25][C:26]1[CH:27]=[C:28]([NH:33][C:34]2[O:24][C:3]([C:4]([NH:6][C:7]3[CH:8]=[CH:9][C:10]([N:13]4[CH2:14][CH2:15][C:16]([CH3:23])([C:19]([O:21][CH3:22])=[O:20])[CH2:17][CH2:18]4)=[N:11][CH:12]=3)=[O:5])=[N:1][N:2]=2)[CH:29]=[CH:30][C:31]=1[F:32]

Participants

Conditions

Temperature: 45 °C

Procedure

To a suspension of methyl 1-(5-{[hydrazino(oxo)acetyl]amino}pyridin-2-yl)-4-methylpiperidine-4-carboxylate (Intermediate 109; 250 mg, 0.75 mmol) in anhydrous DMF (3 mL) was added 3,4-difluorophenylisothiocyanate (154 mg, 0.89 mmol) in anhydrous DMF (1 mL) and the resulting suspension heated to 45° C. for 1 hr. EDAC.HCl (172 mg, 0.89 mmol) was added and the reaction mixture heated to 85° C. for 2 hrs and then allowed to cool to ambient temperature. Water (15 mL) was added and the suspension was filtered, washed with water (2×10 mL) and ether (15 mL) then dried to give the title product as a yellow solid (282 mg, 0.597 mmol, 79.6%);

Workup

temperaturethe reaction mixture heated to 85° C. for 2 hrs
temperatureto cool to ambient temperature
filtrationthe suspension was filtered
washwashed with water (2×10 mL) and ether (15 mL)
customthen dried

Sources & evidence

ORD record: ord-ad916c6866f84027bb9cbb6b930c921d
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795283B2

Reaction notes

Loading…