Trimethylsilyl iodide → HCID 178511031, compound

HRID 1665112Notes

Reaction equation

HRID 1665112 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][C@H:14]1[CH2:18][NH:17]/[C:16](=[N:19]\[C:20]([C:22]2[C:27]([NH2:28])=[N:26][C:25]([NH2:29])=[C:24]([Cl:30])[N:23]=2)=[O:21])/[NH:15]1)C1C=CC=CC=1.I[Si](C)(C)C>C(Cl)Cl>[NH2:10][CH2:11][CH2:12][CH2:13][C@H:14]1[CH2:18][NH:17]/[C:16](=[N:19]\[C:20]([C:22]2[C:27]([NH2:28])=[N:26][C:25]([NH2:29])=[C:24]([Cl:30])[N:23]=2)=[O:21])/[NH:15]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 178508794HCID 178508794, compound

Product 1

HCID 178511031HCID 178511031, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3-{(S)-2-[(E)-3,5-Diamino-6-chloro-pyrazine-2-carbonylimino]-imidazolidin-4-yl}-propyl)-carbamic acid benzyl ester (Ex. 30) (0.44 g, 0.98 mmol) in DCM (20 ml) is added iodotrimethylsilane (0.27 ml, 1.96 mmol) in a dropwise manner. The orange suspension is stirred at room temperature for 65 minutes. Purification by catch and release resin (SCX-2) eluting with MeOH followed by 7M NH3 in MeOH yields the title compound as a yellow foam; [M+H]+ 313.1

Workup

  1. customPurification by catch and release resin (SCX-2)
  2. washeluting with MeOH

Sources & evidence

ORD record
ord-ed9624c2c8574bebbf6c565c4cb68dfa
Source dataset
uspto-grants-2011_10
Patent number
US08039472B2

Reaction notes

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