Trimethylsilyl iodide → HCID 57947533, compound

HRID 416400Notes

Reaction equation

HRID 416400 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12](=[O:40])[O:13][CH2:14][C@@H:15]([N:26]([CH3:39])[C:27]([NH:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:32]=2[F:38])=[O:28])[CH2:16][CH2:17][CH2:18][O:19][P:20]([O:24]C)([O:22]C)=[O:21])[N:2]=1.[Si](I)(C)(C)C>C(#N)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([NH:11][C:12](=[O:40])[O:13][CH2:14][C@@H:15]([N:26]([CH3:39])[C:27]([NH:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[C:32]=2[F:38])=[O:28])[CH2:16][CH2:17][CH2:18][O:19][P:20]([OH:24])([OH:22])=[O:21])[N:2]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 57947544HCID 57947544, compound

Product 1

HCID 57947533HCID 57947533, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S)-2-(3-(2,3-difluorobenzyl)-1-methylureido)-5-(dimethoxyphosphoryloxy)pentyl isoquinolin-3-ylcarbamate (531 mg, 0.91 mmol) in acetonitrile (18 mL) was added TMSI (0.50 mL, 3.66 mmol) at 0° C. After stirred at RT for 10 min, the reaction was quenched with MeOH. The solvent was removed and the resulting residue was purified on RP-HPLC using a mixture of acetonitrile and H2O (0.1% HCOOH buffer) to give (S)-2-(3-(2,3-difluorobenzyl)-1-methylureido)-5-(phosphonooxy)pentyl isoquinolin-3-ylcarbamate (261 mg, 52%). LRMS (M+H+) m/z 553.5.

Workup

  1. customthe reaction was quenched with MeOH
  2. customThe solvent was removed
  3. customthe resulting residue was purified on RP-HPLC
  4. additiona mixture of acetonitrile and H2O (0.1% HCOOH buffer)

Sources & evidence

ORD record
ord-4a672b9320df456998ef58672f4b6819
Source dataset
uspto-grants-2012_01
Patent number
US08088793B2

Reaction notes

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