Trifluoroacetic acid → {3-[2-(4-Methoxy-benzyl)-1,1-dioxo-1,2-dihydro-1lambda6-benzo[e][1,2,3]thiadiazin-4-yl]-5-fluoro-2-methyl-indol-1-yl}-acetic acid

HRID 1013238Notes

Reaction equation

HRID 1013238 reaction equation
C([O:5][C:6](=[O:40])[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][C:34]([O:37][CH3:38])=[CH:33][CH:32]=3)[N:19]=2)=[C:9]1[CH3:39])(C)(C)C.C(O)(C(F)(F)F)=O>>[CH3:38][O:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][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:40])=[O:5])[C:9]=3[CH3:39])[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[S:21]2(=[O:28])=[O:29])=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67316653{3-[2-(4-Methoxy-benzyl)-1,1-dioxo-1,2-dihydro-1lambda6-benzo[e][1,2,3]thiadiazin-4-yl]-5-fluoro-2-methyl-indol-1-yl}-acetic acid tert-butyl ester

Product 1

HCID 11663445{3-[2-(4-Methoxy-benzyl)-1,1-dioxo-1,2-dihydro-1lambda6-benzo[e][1,2,3]thiadiazin-4-yl]-5-fluoro-2-methyl-indol-1-yl}-acetic acid

Procedure

{3-[2-(4-Methoxy-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 8.12 (d, 1H), 7.91 (t, 1H), 7.81 (t, 1H), 7.44 (d, 1H), 7.32 (m, 3H), 6.92 (m, 3H), 6.62 (dd, 1H), 4.99 (bs, 2H), 4.51 (s, 2H.), 3.73 (s, 3H), 2.09 (s, 3H) ppm. MS calculated for C26H22FN3O5S—H: 506, observed: 506.

Workup

  1. concentrationconcentrated
  2. custompurified by preparative LCMS

Sources & evidence

ORD record
ord-52f84cc7c0d049b9995cb5acec3d2f64
Source dataset
uspto-grants-2011_07
Patent number
US07981912B2

Reaction notes

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