Trimethylsilyl iodide → HCID 66622169, compound

HRID 409801Notes

Reaction equation

HRID 409801 reaction equation
[Cl:1][C:2]1[C:44]([F:45])=[CH:43][CH:42]=[CH:41][C:3]=1[CH2:4][NH:5][C:6](=[O:40])[N:7]([CH:9]([CH2:25][O:26][CH2:27][CH:28]([OH:39])[CH2:29][O:30][P:31]([O:36]CC)([O:33]CC)=[O:32])[CH2:10][O:11][C:12](=[O:24])[NH:13][C:14]1[N:15]=[CH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:8].[Si](I)(C)(C)C>C(#N)C>[Cl:1][C:2]1[C:44]([F:45])=[CH:43][CH:42]=[CH:41][C:3]=1[CH2:4][NH:5][C:6](=[O:40])[N:7]([CH:9]([CH2:25][O:26][CH2:27][CH:28]([OH:39])[CH2:29][O:30][P:31]([OH:36])([OH:33])=[O:32])[CH2:10][O:11][C:12](=[O:24])[NH:13][C:14]1[N:15]=[CH:16][C:17]2[C:22]([CH:23]=1)=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:8]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 66622141HCID 66622141, compound

Product 1

HCID 66622169HCID 66622169, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of Isoquinolin-3-yl-carbamic acid 2-[3-(2-chloro-3-fluoro-benzyl)-1-methyl-ureido]-3-[3-(diethoxy-phosphoryloxy)-2-hydroxy-propoxy]-propyl ester (0.60 g, 0.895 mmol) in acetonitrile (30 mL) was added TMSI (1.43 g, 7.16 mmol) dropwise at 0° C. After stirring at 0° C. for 4.5 h, the reaction was quenched with EtOH. The solvent was removed, and the resulting residue was purified on RP-HPLC using a mixture of acetonitrile and H2O (0.1% TFA buffer) to give isoquinolin-3-yl-carbamic acid 2-[3-(2-chloro-3-fluoro-benzyl)-1-methyl-ureido]-3-(2-hydroxy-3-phosphonooxy-propoxy)-propyl ester (396 mg, 73%). LRMS [M−H]+ m/z 613.5

Workup

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

Sources & evidence

ORD record
ord-4c6be4a65b2b4c6b8edaba9f6ac11156
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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