Trifluoroacetic acid → HCID 11626109, compound

HRID 750723Notes

Reaction equation

C([O:5][C:6](=[O:34])[CH2:7][N:8]1[C:16]2[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=2)[C:10]([C:18]2[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[S:21](=[O:29])(=[O:28])[N:20]([CH:30]([CH3:32])[CH3:31])[N:19]=2)=[C:9]1[CH3:33])(C)(C)C.C(O)(C(F)(F)F)=O>>[CH:30]([N:20]1[N:19]=[C:18]([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=3)[N:8]([CH2:7][C:6]([OH:34])=[O:5])[C:9]=2[CH3:33])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[S:21]1(=[O:29])=[O:28])([CH3:32])[CH3:31]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 67316166HCID 67316166, compound

Product 1

HCID 11626109HCID 11626109, compound

Procedure

[3-(2-Isopropyl-1,1-dioxo-1,2-dihydro-1λ6-benzo[e][1,2,3]thiadiazin-4-yl)-5-fluoro-2-methyl-indol-1-yl]-acetic acid tert-butyl ester (61 μmol) was treated with TFA (2 mL) for 2 hours, concentrated, and purified by preparative LCMS to give the title compound. 1H NMR (d6-DMSO) δ 8.08 (d, 1H), 7.90 (t, 1H), 7.83 (t, 1H), 7.47 (m, 2H), 6.97 (m, 2H), 4.71 (m, 1H), 4.53 (s, 2H), 2.23 (s, 3H), 1.47 (m, 6H) ppm. MS calculated for C21H20FN3O4S—H: 428, observed: 428.

Workup

concentrationconcentrated
custompurified by preparative LCMS

Sources & evidence

ORD record: ord-8488587f5053496790b6ceb61487d1de
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405215B2

Reaction notes

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