Morpholine → HCID 44468654, compound

HRID 38981Notes

Reaction equation

CC1C=CC(S(O[CH2:12][C@@H:13]2[O:18][C:17]3[CH:19]=[C:20]([S:24]([CH3:27])(=[O:26])=[O:25])[CH:21]=[C:22]([F:23])[C:16]=3[O:15][CH2:14]2)(=O)=O)=CC=1.[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>C(#N)C>[F:23][C:22]1[C:16]2[O:15][CH2:14][C@H:13]([CH2:12][N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[O:18][C:17]=2[CH:19]=[C:20]([S:24]([CH3:27])(=[O:25])=[O:26])[CH:21]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of [(2R)-5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.39 g, 0.95 mmol), morpholine (0.3 ml, 3.4 mmol) and ACN (3 ml) was heated under microwave radiation at 120° C. for 70 min. Purification on SCX-3 column (TEA/MeOH) and by flash column chromatography and (isooctane/EtOAc/MeOH). Yield: 0.17 g. The amine was converted to the hydrochloric acid salt and crystallized from MeOH/Et2O. M.p. 251° C. MS m/z (rel. intensity, 70 eV) 331 (M+, 1), 207 (2), 101 (6), 100 (bp), 69 (2), 56 (5).

Workup

customPurification on SCX-3 column (TEA/MeOH)
customcrystallized from MeOH/Et2O

Sources & evidence

ORD record: ord-258b468f1594451faaed443785c6be7a
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08524766B2

Reaction notes

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