Bromotrimethylsilane → HCID 67994725, compound

HRID 1431013Notes

Reaction equation

HRID 1431013 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:26]=[C:27]([O:29][C:30]2[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=2)[CH:28]=1)[C:8]([NH:10][C:11]1[CH:16]=[N:15][C:14]([CH2:17][P:18](=[O:25])([O:22]CC)[O:19]CC)=[CH:13][N:12]=1)=[O:9])([CH3:3])[CH3:2].[Br:40][Si](C)(C)C>C(Cl)Cl>[BrH:40].[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:26]=[C:27]([O:29][C:30]2[CH:35]=[CH:34][C:33]([S:36]([CH3:39])(=[O:38])=[O:37])=[CH:32][CH:31]=2)[CH:28]=1)[C:8]([NH:10][C:11]1[N:12]=[CH:13][C:14]([CH2:17][P:18](=[O:19])([OH:22])[OH:25])=[N:15][CH:16]=1)=[O:9])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 76113BromotrimethylsilaneHCID 58528998HCID 58528998, compound

Product 1

HCID 67994725HCID 67994725, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a similar manner to Example 1, a mixture of diethyl {2-[3-isopropoxy-5-(4-methanesulfonyl-phenoxy)-benzoylamino]-pyrazin-5-ylmethyl}phosphonate (29 mg, 0.05 mmol) and bromotrimethylsilane (0.13 mL, 1.0 mmol) in 1 mL of CH2Cl2 was stirred for 16 h at rt and the solvents evaporated. The residue was sonicated in 1 mL of CH3CN, the solvent evaporated, the residue sonicated in 1 mL CH3CN and 2 mL water, the solution concentrated by evaporation followed by lyophilization to provide 28 mg (76%) of the title compound as an amorphous solid. 1H NMR (500 MHz, DMSO-d6): δ 1.31 (d, 6H, J=6 Hz), 3.21 (s, 3H), 3.23 (d, 2H, J=22 Hz), 4.78 (septet, 1H, J=6 Hz), 6.97 (t, 1H, J=2 Hz), 7.25 (d, 2H, J=8 Hz), 7.36 (t, 1H, J=2 Hz), 7.52 (t, 1H, J=2 Hz), 7.95 (d, 2H, J=8 Hz), 8.39 (t, 1H, J=2 Hz), 9.25 (d, 1H, J=1 Hz), 11.13 (s, 1H); LCMS (m/z): 522.4 [C22H24N3O8PS+H]+. Anal. calcd. for (C22H24N3O8PS+2HBr+3H2O): C, 35.84; H, 4.37; N, 5.70. Found: C, 35.59; H, 4.19; N, 5.41.

Workup

  1. customthe solvents evaporated
  2. customThe residue was sonicated in 1 mL of CH3CN
  3. customthe solvent evaporated
  4. customthe residue sonicated in 1 mL CH3CN
  5. concentration2 mL water, the solution concentrated by evaporation

Sources & evidence

ORD record
ord-90ca99ef6ca94d77b2c3e6ee0ef6193f
Source dataset
uspto-grants-2015_01
Patent number
US08940927B2

Reaction notes

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