Triethylsilane → HCID 9849678, compound

HRID 1251321Notes

Reaction equation

HRID 1251321 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:14][CH2:13][N:12]([CH2:15][CH2:16][NH:17][C:18](=[O:37])[CH2:19][CH2:20][N:21]2[CH2:26][CH:25]=[C:24]([C:27]3[C:35]4[C:30](=[CH:31][C:32]([Cl:36])=[CH:33][CH:34]=4)[NH:29][CH:28]=3)[CH2:23][CH2:22]2)[CH2:11][CH2:10]1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O.ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH2:10][CH2:11][N:12]([CH2:15][CH2:16][NH:17][C:18](=[O:37])[CH2:19][CH2:20][N:21]2[CH2:22][CH2:23][CH:24]([C:27]3[C:35]4[C:30](=[CH:31][C:32]([Cl:36])=[CH:33][CH:34]=4)[NH:29][CH:28]=3)[CH2:25][CH2:26]2)[CH2:13][CH2:14]1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 9849614HCID 9849614, compound

Product 1

HCID 9849678HCID 9849678, compoundYield 95.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of the compound of EXAMPLE 2 (0.383 mmol) and triethylsilane (0.422 mmol) in trifluoroacetic acid (6 ML) was stirred at 0° C. for 2.5 hours. The mixture was diluted with dichloromethane (20 mL) and quenched with sodium hydroxide solution until the pH was 10-13. The mixture was extracted with dichloromethane, dried over magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography using 8% methanol, 0.5% ammonium hydroxide in dichloromethane to give the title compound (191 mg, 95%).

Workup

  1. customquenched with sodium hydroxide solution until the pH was 10-13
  2. extractionThe mixture was extracted with dichloromethane
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-bdff840ce5de461098d229cb186155c1
Source dataset
uspto-grants-2002_01
Patent number
US06342498B1

Reaction notes

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