Trifluoroacetic acid → 2-[4-(2-Aminoethyl)-2-pyridyl]-4h-1,3-benzothiazine-4-one trifluoroacetic acid salt

HRID 499490Notes

Reaction equation

[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[S:5][C:4]([C:12]2[CH:17]=[C:16]([CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)[CH:15]=[CH:14][N:13]=2)=[N:3]1.[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31]>>[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31].[NH2:20][CH2:19][CH2:18][C:16]1[CH:15]=[CH:14][N:13]=[C:12]([C:4]2[S:5][C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=3[C:2](=[O:1])[N:3]=2)[CH:17]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 22939473HCID 22939473, compound

Product 1

HCID 684561462-[4-(2-Aminoethyl)-2-pyridyl]-4h-1,3-benzothiazine-4-one trifluoroacetic acid saltYield 89%

Procedure

tert-Butyl 2-[2-(4-oxo-4H-1,3-benzothiazin-2-yl)-4-pyridyl]ethylcarbamate (0.82 g, 2.1 mmol) was dissolved in trifluoroacetic acid (10 ml), and the mixture was stirred at room temperature for 2 hrs. The solvent was evaporated, and the residue was recrystallized from methanol-diisopropyl ether to give the titled compound (0.75 g, 89%) as white crystals.

Workup

customThe solvent was evaporated
customthe residue was recrystallized from methanol-diisopropyl ether

Sources & evidence

ORD record: ord-7c940a50a58c4bda9b3f0d123ae0e1e1
Source dataset: uspto-grants-2010_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07767665B2

Reaction notes

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