Triethylsilane → HCID 71558621, compound

HRID 2203435Notes

Reaction equation

HRID 2203435 reaction equation
C([C:5]1[C:10]2[C:11]([N:14](C3C4C(C(C)(C)C)=C(C5C=C(Cl)C=CC=5OC5C=C(F)C(S(=O)(=O)N(C6N=CC=CN=6)CC6C=CC=CC=6)=CC=5F)C=CC=4ON=3)C(=O)[O-])=[N:12][O:13][C:9]=2[CH:8]=[CH:7][C:6]=1[C:64]1[CH:69]=[C:68]([Cl:70])[CH:67]=[CH:66][C:65]=1[O:71][C:72]1[CH:77]=[C:76]([F:78])[C:75]([S:79](=[O:95])(=[O:94])[N:80](CC2C=CC=CC=2)[C:81]2[N:86]=[CH:85][CH:84]=[CH:83][N:82]=2)=[CH:74][C:73]=1[F:96])(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)S(O)(=O)=O>FC(F)(F)C(O)=O>[NH2:14][C:11]1[C:10]2[CH:5]=[C:6]([C:64]3[CH:69]=[C:68]([Cl:70])[CH:67]=[CH:66][C:65]=3[O:71][C:72]3[C:73]([F:96])=[CH:74][C:75]([S:79]([NH:80][C:81]4[N:86]=[CH:85][CH:84]=[CH:83][N:82]=4)(=[O:94])=[O:95])=[C:76]([F:78])[CH:77]=3)[CH:7]=[CH:8][C:9]=2[O:13][N:12]=1

Participants

5

Reactant 3

HCID 12052TriethylsilaneHCID 62406Trifluoromethanesulfonic acidHCID 90389211HCID 90389211, compound

Product 1

HCID 71558621HCID 71558621, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of bis(tert-butyl (5-(2-(4-(N-benzyl-N-(pyrimidin-2-yl)sulfamoyl)-2,5-difluorophenoxy)-5-chlorophenyl)benzo[d]isoxazol-3-yl))carbamate (2.03 g, 2.47 mmol) in trifluoroacetic acid (50 mL) were added triethylsilane (2.0 mL, 13 mmol) and trifluoromethanesulfonic acid (0.5 mL). This mixture was heated at reflux for 5 h and allowed to cool to ambient temperature. The mixture was concentrated in vacuo to afford a brown residue that was triturated in diethyl ether (40 mL) to afford 4-(2-(3-aminobenzo[d]isoxazol-5-yl)-4-chlorophenoxy)-2,5-difluoro-N-(pyrimidin-2-yl)benzenesulfonamide as an off-white solid in 72% yield (0.95 g): 1H NMR (300 MHz, 5% D2O in DMSO-d6) δ 8.35 (d, J=4.9 Hz, 2H), 7.90 (s, 1H), 7.72 (dd, J=9.9, 6.6 Hz, 1H), 7.58-7.55 (m, 2H), 7.47 (dd, J=8.7, 2.3, 1H), 7.37 (d, J=8.7 Hz, 1H), 7.25 (d, J=8.7 Hz, 1H), 6.96 (t, J=4.8 Hz, 1H), 6.90 (dd, J=10.3, 6.6 Hz, 1H) (NH not observed); MS (ES+) m/z 529.6 (M+1), 531.5 (M+1).

Workup

  1. temperatureThis mixture was heated
  2. temperatureat reflux for 5 h
  3. concentrationThe mixture was concentrated in vacuo
  4. customto afford a brown residue that
  5. customwas triturated in diethyl ether (40 mL)

Sources & evidence

ORD record
ord-1f9749a8723148e4ade12228916a3110
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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