Methyl iodide → HCID 178497765, compound

HRID 77519Notes

Reaction equation

HRID 77519 reaction equation
[CH3:1][O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[CH2:16][CH2:15][CH2:14][C@H:13]([NH:17][C:18]([NH2:31])=[N:19][C:20]([C:22]3[C:27]([NH2:28])=[N:26][C:25]([NH2:29])=[C:24]([Cl:30])[N:23]=3)=[O:21])[CH2:12]2)[CH:5]=1.[CH3:33]I>CC(C)=O.CN(C)C=O>[Cl-:30].[NH2:28][C:27]1[C:22]([C:20]([N:19]=[C:18]([NH2:31])[NH:17][CH:13]2[CH2:14][CH2:15][CH2:16][N@+:11]([CH2:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([C:3]([O:2][CH3:1])=[O:32])[CH:5]=3)([CH3:33])[CH2:12]2)=[O:21])=[N:23][C:24]([Cl:30])=[C:25]([NH2:29])[N:26]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 178497766HCID 178497766, compound2×

Product 1

HCID 178497765HCID 178497765, compound

Reagents, catalysts & solvents 1

HCID 18184436N,N-dimethylformamide acetoneSolvent

Procedure

A mixture of 35 mg (0.066 mmol) (S)-3-{3-[N′-(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-guanidino]-piperidin-1-ylmethyl}-benzoic acid methyl ester (intermediate 10) and 100 μl (0.7 mmol) methyl iodide in 2 ml acetone/dimethylformamide (1:1) is stirred at room temperature overnight. Then the reaction mixture is concentrated under reduced pressure and the residue is purified by preparative reverse phase HPLC (gradient of methanol and water+0.2% trifluoroacetic acid, 25° C.). Fractions containing the title compound were concentrated under reduced pressure, treated with excess HCl in methanol and evaporated again.

Workup

  1. concentrationThen the reaction mixture is concentrated under reduced pressure
  2. customthe residue is purified by preparative reverse phase HPLC (gradient of methanol and water+0.2% trifluoroacetic acid, 25° C.)
  3. additionFractions containing the title compound
  4. concentrationwere concentrated under reduced pressure
  5. additiontreated with excess HCl in methanol
  6. customevaporated again

Sources & evidence

ORD record
ord-b3a2864b3cac4a5590bfc4b2757fc0c9
Source dataset
uspto-grants-2014_09
Patent number
US08841309B2

Reaction notes

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