Triethylsilane → HCID 71559073, compound

HRID 2203453Notes

Reaction equation

HRID 2203453 reaction equation
C([N:14]1[C:18]2[CH:19]=[C:20]([C:23]3[CH:57]=[C:56]([CH3:58])[CH:55]=[CH:54][C:24]=3[O:25][C:26]3[C:31]([F:32])=[CH:30][C:29]([S:33]([N:36](CC4C=CC(OC)=CC=4OC)[C:37]4[S:41][N:40]=[CH:39][N:38]=4)(=[O:35])=[O:34])=[C:28]([F:53])[CH:27]=3)[CH:21]=[CH:22][C:17]=2[O:16][C:15]1=[O:59])(C1C=CC=CC=1)C1C=CC=CC=1.C([SiH](CC)CC)C.FC(F)(F)S(O)(=O)=O>FC(F)(F)C(O)=O>[F:53][C:28]1[CH:27]=[C:26]([O:25][C:24]2[CH:54]=[CH:55][C:56]([CH3:58])=[CH:57][C:23]=2[C:20]2[CH:21]=[CH:22][C:17]3[O:16][C:15](=[O:59])[NH:14][C:18]=3[CH:19]=2)[C:31]([F:32])=[CH:30][C:29]=1[S:33]([NH:36][C:37]1[S:41][N:40]=[CH:39][N:38]=1)(=[O:34])=[O:35]

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 62406Trifluoromethanesulfonic acidHCID 90389188HCID 90389188, compound

Product 1

HCID 71559073HCID 71559073, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a mixture of 4-(2-(3-benzhydryl-2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)-4-methylphenoxy)-N-(2,4-dimethoxybenzyl)-2,5-difluoro-N-(1,2,4-thiadiazol-5-yl)benzene-sulfonamide (0.93 g, 1.11 mmol) in trifluoroacetic acid (10 mL) and triethylsilane (1.44 mL, 8.9 mmol) was added trifluoromethanesulfonic acid (0.5 mL, 5.7 mmol). The reaction mixture was heated under at reflux for 0.5 h, allowed to cool to ambient temperature and concentrated in vacuo. The residue was purified by column chromatography eluting with a 20-100% gradient of ethyl acetate in hexanes followed by trituration in methanol (3 mL) to afford 2,5-difluoro-4-(4-methyl-2-(2-oxo-2,3-dihydrobenzo[d]oxazol-5-yl)phenoxy)-N-(1,2,4-thiadiazol-5-yl)benzenesulfonamide as a light pink solid in 22% yield (0.13 g): 1H NMR (300 MHz, DMSO-d6) δ 11.67 (s, 1H), 8.53 (s, 1H), 7.72 (dd, J=10.0, 6.4 Hz, 1H), 7.34 (d, J=1.8 Hz, 1H), 7.29 (d, J=8.9 Hz, 1H), 7.27-7.23 (m, 1H), 7.17-7.11 (m, 3H), 6.90 (dd, J=10.6, 6.5 Hz, 1H), 2.37 (s, 3H), (NH not observed); MS (ES+) m/z 516.6 (M+1).

Workup

  1. temperatureThe reaction mixture was heated under
  2. temperatureat reflux for 0.5 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography
  5. washeluting with a 20-100% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-5fff7d10c75b4166a877234a872edca1
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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