Methanol → HCID 178510993, compound

HRID 2365543Notes

Reaction equation

HRID 2365543 reaction equation
C(OC(=O)[NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]1[CH2:19][NH:18]/[C:17](=[N:20]\[C:21]([C:23]2[C:28]([NH2:29])=[N:27][C:26]([NH2:30])=[C:25]([Cl:31])[N:24]=2)=[O:22])/[NH:16]1)C1C=CC=CC=1.I[Si](C)(C)C.CO>C(Cl)Cl>[NH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]1[CH2:19][NH:18]/[C:17](=[N:20]\[C:21]([C:23]2[C:28]([NH2:29])=[N:27][C:26]([NH2:30])=[C:25]([Cl:31])[N:24]=2)=[O:22])/[NH:16]1

Participants

5

Reactant 3

HCID 887MethanolHCID 85247Trimethylsilyl iodideHCID 178508790HCID 178508790, compound

Product 1

HCID 178510993HCID 178510993, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of (4-{(S)-2-[(E)-3,5-Diamino-6-chloro-pyrazine-2-carbonylimino]-imidazolidin-4-yl}-butyl)-carbamic acid benzyl ester (Ex. 5) (0.110 g, 0.239 mmol) in dry DCM (20 ml) is added iodotrimethylsilane (0.130 ml, 0.956 mmol). The reaction mixture is stirred at room temperature for 3.5 hours. MeOH is added to the suspension yielding a solution. Purification by catch and release resin (SCX-2) eluting with MeOH and 7 M NH3 in MeOH yields the title compound as a brown oil; [M+H]+ 327.1

Workup

  1. customyielding a solution
  2. customPurification by catch and release resin (SCX-2)
  3. washeluting with MeOH and 7 M NH3 in MeOH

Sources & evidence

ORD record
ord-70f8500d714640bba1a33f9ddc49bdae
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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