Acetic Acid → 2-(((4-amino-2,2-dioxido-1H-benzo[c][1,2,6]thiadiazin-5-yl)oxy)methyl)-N-ethylpiperidine-1-carboxamide

HRID 1483964Notes

Reaction equation

[C:1]([C:3]1[C:21]([NH:22][S:23](=[O:26])(=[O:25])[NH2:24])=[CH:20][CH:19]=[CH:18][C:4]=1[O:5][CH2:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[C:13]([NH:15][CH2:16][CH3:17])=[O:14])#[N:2].[OH-].[Na+].CC(O)=O>CCO.O>[NH2:2][C:1]1[C:3]2[C:4]([O:5][CH2:6][CH:7]3[CH2:12][CH2:11][CH2:10][CH2:9][N:8]3[C:13]([NH:15][CH2:16][CH3:17])=[O:14])=[CH:18][CH:19]=[CH:20][C:21]=2[NH:22][S:23](=[O:25])(=[O:26])[N:24]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 2-((2-cyano-3-(sulfamoylamino)phenoxy)methyl)-N-ethylpiperidine-1-carboxamide (Example 26a, 0.6 g, 1.57 mmol) in EtOH (10 mL) was added NaOH 2M (1.57 mL, 1.57 mmol) and the reaction mixture was heated at 100° C. for 2 h. The solution was then evaporated to dryness. The residue was diluted with water (7.0 mL), and 10% AcOH (3.5 mL, 3.5 mmol) was added at 0° C. to provide a white precipitate which was filtered and washed with cold water and further purified by Biotage purification system (120 g Silicycle column, DCM:THF=4:1 as eluent) to give the title compound (0.318 g, 53%). MS 382 (MH+).

Workup

customThe solution was then evaporated to dryness
additionwas added at 0° C.
customto provide a white precipitate which
filtrationwas filtered
washwashed with cold water
customfurther purified by Biotage purification system (120 g Silicycle column, DCM:THF=4:1 as eluent)

Sources & evidence

ORD record: ord-6909de163fdc42f090616f941933c0f3
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09420814B2

Reaction notes

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