Dimethylformamide → HCID 178508756, compound

HRID 2281589Notes

Reaction equation

HRID 2281589 reaction equation
I[Si](C)(C)C.[NH2:6][C:7]1[C:8]([C:15](/[N:17]=[C:18]2\[NH:19][CH2:20][C:21]3([CH2:28][CH:27]4[N:29](C(OC(C)(C)C)=O)[CH:24]([CH2:25][CH2:26]4)[CH2:23]3)[NH:22]\2)=[O:16])=[N:9][C:10]([Cl:14])=[C:11]([NH2:13])[N:12]=1.CN(C=O)C>C(Cl)Cl>[NH2:6][C:7]1[C:8]([C:15](/[N:17]=[C:18]2\[NH:19][CH2:20][C:21]3([CH2:28][CH:27]4[NH:29][CH:24]([CH2:25][CH2:26]4)[CH2:23]3)[NH:22]\2)=[O:16])=[N:9][C:10]([Cl:14])=[C:11]([NH2:13])[N:12]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 85247Trimethylsilyl iodide2×HCID 178451396HCID 178451396, compound

Product 1

HCID 178508756HCID 178508756, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Iodotrimethylsilane (0.23 ml, 1.66 mmol) is added to a suspension of (E)-tert-Butyl 2′-(3,5-diamino-6-chloropyrazine-2-carbonylimino)-8-azaspiro[bicyclo[3.2.1]octane-3,4′-imidazolidine]-8-carboxylate (Ex. 251) (500 mg, 1.11 mmol) in DCM (10 ml). DMF (5 ml) is then added and the reaction is stirred at room temperature overnight. Iodotrimethylsilane (0.5 ml) is added and the reaction mixture is concentrated in vacuo. The yellow solid is suspended in DCM and collected by filtration. The solid is dissolved in 1:1 MeOH/DCM and loaded onto an SCX-2 cartridge eluted with DCM followed by MeOH and NH3/MeOH. The methanolic ammonia fractions are concentrated in vacuo to afford (E)-3,5-diamino-6-chloro-N-(8-azaspiro[bicyclo[3.2.1]octane-3,4′-imidazolidine]-2′-ylidene)pyrazine-2-carboxamide as a yellow gum; [M+H]+ 351

Workup

  1. concentrationthe reaction mixture is concentrated in vacuo
  2. filtrationcollected by filtration
  3. dissolutionThe solid is dissolved in 1:1 MeOH/DCM
  4. washeluted with DCM
  5. concentrationThe methanolic ammonia fractions are concentrated in vacuo

Sources & evidence

ORD record
ord-1d7f11b0bff847dab22e018b4a91faa3
Source dataset
uspto-grants-2015_09
Patent number
US09139586B2

Reaction notes

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