Sodium Carbonate → 6-methoxy-2-methyl-3-[(3S,9aR)-octahydropyrazino[2,1-c][1,4]oxazin-3-yl]benzonitrile

HRID 2175897Notes

Reaction equation

FC(F)(F)[C:3](O)=[O:4].F[C:9]1[C:14]([C:15]#[N:16])=[C:13]([CH3:17])[C:12]([C@@H:18]2[O:23][CH2:22][C@H:21]3[CH2:24][NH:25][CH2:26][CH2:27][N:20]3[CH2:19]2)=[CH:11][CH:10]=1.C(=O)([O-])[O-].[Na+].[Na+]>CO>[CH3:3][O:4][C:9]1[C:14]([C:15]#[N:16])=[C:13]([CH3:17])[C:12]([C@@H:18]2[O:23][CH2:22][C@H:21]3[CH2:24][NH:25][CH2:26][CH2:27][N:20]3[CH2:19]2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A microwave vial was charged with 6-fluoro-2-methyl-3-[(3S,9aR)-octahydropyrazino[2,1-c][1,4]oxazin-3-yl]benzonitrile trifluoroacetate (110 mg, 0.290 mmol), sodium carbonate (30 mg, 0.290 mmol), and methanol (2 mL). The mixture was heated to 150° C. in a microwave apparatus for 2 h, then cooled to ambient temperature, filtered and concentrated to provide the title compound which was used without further purification. LC-MS (IE, m/z): 288 [M+1]+.

Workup

temperaturecooled to ambient temperature
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-0845fe58979e4325bfa446a228a7f342
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062070B2

Reaction notes

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