Potassium Carbonate → HCID 86681736, compound

HRID 571323Notes

Reaction equation

[CH3:1][S:2]([NH:5][C:6]1[CH:20]=[CH:19][C:9]2[N:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:11](=[O:13])[O:12][C:8]=2[CH:7]=1)(=[O:4])=[O:3].Cl.Cl[CH2:23][CH2:24][N:25]1[CH2:30][CH2:29][O:28][CH2:27][CH2:26]1.C([O-])([O-])=O.[K+].[K+]>CC#N>[O:28]1[CH2:29][CH2:30][N:25]([CH2:24][CH2:23][N:5]([C:6]2[CH:20]=[CH:19][C:9]3[N:10]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:11](=[O:13])[O:12][C:8]=3[CH:7]=2)[S:2]([CH3:1])(=[O:3])=[O:4])[CH2:26][CH2:27]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of methyl 2-(6-(methylsulfonamido)-2-oxobenzo[d]oxazol-3(2H)-yl)acetate (300 mg, 0.999 mmol) (prepared in an analogous manner as described in Example 24, Scheme 24, Steps 1, 2, 3) in CH3CN (15 ml), 4-(2-chloroethyl)morpholine hydrochloride (186 mg, 0.999 mmol) and K2CO3 (138 mg, 0.999 mmol) were added. The mixture was heated at 100° C. under microwaves irradiation for 1 hour. The solvent was removed under vacuum, and the residue was portioned between EtOAc and water. The organic phase was washed several times with brine and dried over sodium sulfate; the solvent was evaporated to dryness and the crude was purified by flash chromatography on silica gel (DCM/MeOH 98/2) to afford methyl 2-(6-(N-(2-morpholinoethyl)methylsulfonamido)-2-oxobenzo[d]oxazol-3(2H)-yl)acetate (340 mg, 0.822 mmol, 82% yield, MS/ESI+ 414.0 [MH]+).

Workup

customThe solvent was removed under vacuum
washThe organic phase was washed several times with brine
dry with materialdried over sodium sulfate
customthe solvent was evaporated to dryness
customthe crude was purified by flash chromatography on silica gel (DCM/MeOH 98/2)

Sources & evidence

ORD record: ord-49aa603c7b9348b4ad550740a40205c7
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09024027B2

Reaction notes

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