Trifluoroacetic acid → HCID 11511116, compound

HRID 750725Notes

Reaction equation

C([O:5][C:6](=[O:37])[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]3[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]3)[N:19]=2)=[C:9]1[CH3:36])(C)(C)C.C(O)(C(F)(F)F)=O>>[CH:30]1([N:20]2[N:19]=[C:18]([C:10]3[C:11]4[C:16](=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=4)[N:8]([CH2:7][C:6]([OH:37])=[O:5])[C:9]=3[CH3:36])[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[S:21]2(=[O:29])=[O:28])[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 67315056HCID 67315056, compound

Product 1

HCID 11511116HCID 11511116, compound

Procedure

[3-(2-Cyclohexyl-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), 7.88 (t, 1H), 7.81 (t, 1H), 7.42 (m, 2H), 6.91 (m, 2H), 4.55 (s, 2H), 4.29 (m, 1H), 2.23 (s, 3H), 1.88 (m, 5H), 1.65 (m, 2H), 1.47 (m, 2H), 1.11 (m, 1H) ppm. MS calculated for C24H24FN3O4S—H: 468, observed: 468.

Workup

concentrationconcentrated
custompurified by preparative LCMS

Sources & evidence

ORD record: ord-149f219ea60f49ebb957fd4ae5293aa3
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405215B2

Reaction notes

Loading…