Trifluoroacetic acid → HCID 59753832, compound

HRID 750707Notes

Reaction equation

HRID 750707 reaction equation
C([O:5][C:6](=[O:42])[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]([CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[CH:32]=3)[N:19]=2)=[C:9]1[CH3:41])(C)(C)C.C(O)(C(F)(F)F)=O>>[F:39][C:37]([F:38])([F:40])[C:33]1[CH:32]=[C:31]([CH:36]=[CH:35][CH:34]=1)[CH2:30][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:42])=[O:5])[C:9]=2[CH3:41])[C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=2[S:21]1(=[O:28])=[O:29]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67316011HCID 67316011, compound

Product 1

HCID 59753832HCID 59753832, compound

Procedure

{3-[2-(3-Trifluoromethyl-benzyl)-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 8.18 (d, 1H), 7.95 (t, 1H), 7.86 (t, 1H), 7.70 (m, 4H), 7.48 (d, 1H), 7.37 (dd, 1H), 6.89 (dt, 1H), 6.52 (dd, 1H), 5.18 (bs, 2H), 4.48 (s, 2H), 2.07 (s, 3H) ppm. MS calculated for C26H19F4N3O4S—H: 544, observed: 544.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-781195dd4ad0444a8fd4ba08fba477f6
Source dataset
uspto-grants-2008_07
Patent number
US07405215B2

Reaction notes

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