Acetonitrile → 5-Chloro-N-({3-[3-fluoro-4-(3-oxo-4-morpholinyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)-2-thiophenecarboxamide

HRID 2103442Notes

Reaction equation

[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][CH:11]([OH:28])[CH2:12][NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][C:21]3=[O:26])=[C:16]([F:27])[CH:15]=2)=[O:8])=[CH:4][CH:3]=1.[C:29](=C1N=CC=N1)=[O:30].CN(C1C=CC=CN=1)C.C(#N)C>O1CCOCC1>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][CH:11]2[O:28][C:29](=[O:30])[N:13]([C:14]3[CH:19]=[CH:18][C:17]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][C:21]4=[O:26])=[C:16]([F:27])[CH:15]=3)[CH2:12]2)=[O:8])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 180 °C

Procedure

260 mg (0.608 mmol) of 5-chloro-N-(3-{[3-fluoro-4-(3-oxo-4-morpholinyl)phenyl]-amino}-2-hydroxypropyl)-2-thiophenecarboxamide (from Example 61), 197 mg (1.22 mmol) of carbonylimidazole and 7 mg of dimethylaminopyridine in 20 ml of dioxane are boiled under reflux for 5 hours. 20 ml of acetonitrile are then added, and the mixture is stirred in a closed vessel in a microwave oven at 180° C. for 30 minutes. The solution is concentrated using a rotary evaporator and chromatographed on an RP-HPLC column. This gives 53 mg (19% of theory) of the target compound.

Workup

temperatureunder reflux for 5 hours
concentrationThe solution is concentrated
customa rotary evaporator
customchromatographed on an RP-HPLC column

Sources & evidence

ORD record: ord-9e29f7fd7e824ed19270125cc4d82ca5
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576111B2

Reaction notes

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