Chlorotrimethylsilane → HCID 68593660, compound

HRID 2191064Notes

Reaction equation

HRID 2191064 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]1[O:15][CH:14]([CH2:16][CH:17]([P:26](=[O:29])([OH:28])[OH:27])S(C2C=CC=CC=2)=O)[CH:13]([F:30])[CH:12]1[OH:31].C(N(CCCC)CCCC)CCC.C[Si](Cl)(C)C>CN(C=O)C>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:11]1[O:15][CH:14]([CH:16]=[CH:17][P:26](=[O:27])([OH:28])[OH:29])[CH:13]([F:30])[CH:12]1[OH:31]

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 7622TributylamineHCID 68593093HCID 68593093, compound

Product 1

HCID 68593660HCID 68593660, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

Compound 49.4 (147 mg, 0.31 mmol) was dissolved in anhydrous DMF, treated with tributylamine (1.49 mL, 6.24 mmol) and TMSCl (0.79 mL, 6.24 mmol). The mixture was heated to 130° C. for 4 h and then cooled to rt. The reaction was quenched with water and stirred at rt for another 2 h. The mixture was concentrated under reduced pressure and the residue was washed with acetonitrile. The acetonitrile washes were discarded and the residue was dissolved in water, subjected to a reverse phase HPLC to give compound 49.5 (34 mg, 24% yield). 1H NMR (D2O, 300 MHz): δ 4.91-5.17 (m, 3H), 5.92-5.95 (m, 1H), 6.07-6.59 (m, 2H), 8.37 (s, 1H). 31PNMR: 11.82 ppm. LRMS [M−H]− C11H13FN5O5P requires 344.1. Found 344.1.

Workup

  1. temperaturecooled to rt
  2. customThe reaction was quenched with water
  3. concentrationThe mixture was concentrated under reduced pressure
  4. washthe residue was washed with acetonitrile
  5. dissolutionthe residue was dissolved in water

Sources & evidence

ORD record
ord-168fe75088b64fe89996c55f9f50244d
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

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