Hydrochloric Acid → 4-(2,2-Dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl)phenol

HRID 1748010Notes

Reaction equation

[Si]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[C:20]3=[N:21][S:22](=[O:26])(=[O:25])[CH2:23][CH2:24][N:19]3[CH2:18][CH2:17][CH2:16]2)=[CH:11][CH:10]=1)(C(C)(C)C)(C)C.Cl>CC(O)=O>[O:26]=[S:22]1(=[O:25])[CH2:23][CH2:24][N:19]2[CH2:18][CH2:17][CH2:16][CH:15]([C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=3)[C:20]2=[N:21]1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 9-(4-((tert-butyldimethylsilyl)oxy)phenyl)-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide (6.97 g) and 6 M HCl aq. (10.0 mL) in AcOH (100 mL) was stirred at 60° C. for 2 hr. After cooling to room temperature, the solvent was removed in vacuo. The residual solid was recrystallized from MeOH-IPE to give the title compound (5.01 g) as a white solid.

Workup

temperatureAfter cooling to room temperature
customthe solvent was removed in vacuo
customThe residual solid was recrystallized from MeOH-IPE

Sources & evidence

ORD record: ord-ca85ea92bfdb45f8b09eaefa3d083aee
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09150591B2

Reaction notes

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