Propionyl chloride → Methyl 4-{5-[3-(propionylamino)-4-(2-methylpiperidin-1-yl)phenyl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate

HRID 219948Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]([F:30])[CH:21]=3)[N:16]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH3:14].[C:31](Cl)(=[O:34])[CH2:32][CH3:33]>C(Cl)Cl.N1C=CC=CC=1>[C:31]([NH:1][C:2]1[CH:3]=[C:4]([C:15]2[O:19][N:18]=[C:17]([C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[C:22]([F:30])[CH:21]=3)[N:16]=2)[CH:5]=[CH:6][C:7]=1[N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH3:14])(=[O:34])[CH2:32][CH3:33]

Participants

Conditions

Temperature: 40 °C

Procedure

Methyl 4-{5-[3-amino-4-(2-methylpiperidin-1-yl)phenyl]-1,2,4-oxadiazol-3-yl}-2-fluorobenzoate, prepared as in example 67, Steps 1 and 2, (100 mg; 0.24 mmol) was suspended in a DCM/Pyridine mixture (4 mL, 1:1). Propionyl chloride (25 μL, 0.29 mmol) was added and the mixture was heated to 40° C. for 18 h. After this time, solvents were removed under vacuum and title compound was obtained as an off-white powder after trituration with MeOH (96 mg; 83%). LC/MS (Method B): 467.4 (M+H)+. HPLC (Method A) Rt. 5.69 min (purity: 93.6%).

Workup

customAfter this time, solvents were removed under vacuum

Sources & evidence

ORD record: ord-872dc886a2c145b5b233ecf103bf9759
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202865B2

Reaction notes

Loading…