Trifluoroacetic acid → HCID 86594444, compound

HRID 915173Notes

Reaction equation

[C:1]1([C:7]2[S:11][C:10]([NH:12][C:13]([N:15]3[CH2:21][CH2:20][CH2:19][N:18](C(OC(C)(C)C)=O)[CH2:17][CH2:16]3)=[O:14])=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:29][C:30]([F:35])([F:34])[C:31]([OH:33])=[O:32]>>[F:29][C:30]([F:35])([F:34])[C:31]([O-:33])=[O:32].[C:1]1([C:7]2[S:11][C:10]([NH:12][C:13]([N:15]3[CH2:21][CH2:20][CH2:19][NH2+:18][CH2:17][CH2:16]3)=[O:14])=[N:9][CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 58958446HCID 58958446, compound

Product 1

HCID 86594444HCID 86594444, compound

Procedure

tert-butyl 4-{[(5-phenyl-1,3-thiazol-2-yl)amino]carbonyl}-1,4-diazepane-1-carboxylate (211.0 mg, 0.52 mmol) was treated with trifluoroacetic acid (2.0 ml) for fifteen minutes. The solvent was removed and the residue put under high vacuum to afford 4-{[(5-phenyl-1,3-thiazol-2-yl)amino]carbonyl}-1,4-diazepan-1-ium trifluoroacetate 25. 1H-NMR (500 MHz, DMSO-d6): 8.73 (1H, br s), 8.68 (1H, br s) 7.78 (1H, s), 7.57 (2H, d, J=7.57), 7.40 (2H, t, J=7.57), 7.28 (1H, t, J=7.57), 3.76 (2H, br s), 3.63 (2H, br s), 3.21 (4H, br s), 1.98 (2H, br m). High res. ES MS: Theoretical Mass 303.1274, Measured Mass 303.1276(C15H19N4OS+H+)

Workup

customThe solvent was removed

Sources & evidence

ORD record: ord-06161ee2123f4863afe00a61c5662341
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07265134B2

Reaction notes

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