Methanol → HCID 178510993, compound

HRID 2281615Notes

Reaction equation

HRID 2281615 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-4a7bab14863048008e2761a6e49fa73a
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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