Methyl iodide → HCID 86656627, compound

HRID 882889Notes

Reaction equation

HRID 882889 reaction equation
[CH2:1]([CH:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][NH:16][C:17]([C:19]2[C:24]([NH2:25])=[N:23][C:22]([NH2:26])=[C:21]([Cl:27])[N:20]=2)=[O:18])[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][I:29]>CC(C)=O>[I-:29].[CH2:1]([CH:8]1[CH2:9][CH2:10][N+:11]([CH2:14][CH2:15][NH:16][C:17]([C:19]2[C:24]([NH2:25])=[N:23][C:22]([NH2:26])=[C:21]([Cl:27])[N:20]=2)=[O:18])([CH3:28])[CH2:12][CH2:13]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 86656628HCID 86656628, compound

Product 1

HCID 86656627HCID 86656627, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid [2-(4-benzyl-piperidin-1-yl)-ethyl]-amide (39 mg, 0.10 mmol) and methyl iodide (0.031 mL, 0.50 mmol) in acetone (2 mL) is heated at reflux for 3 h. After cooling to RT the solvent is removed in vacuo to afford the title compound as yellow solid. M+ 403. 1H NMR (400 MHz, DMSO-d6) δ 8.30 (1H, t), 7.62 (2H, br), 7.39-7.36 (2H, m), 7.29-7.23 (3H, m), 7.16 (2H, br), 3.73-3.47 (6H, m), 3.35-3.28 (2H, m), 3.14 (3H, s), 2.67 (2H, d), 1.92-1.81 (1H, m), 1.74-1.68 (4H, m).

Workup

  1. temperatureat reflux for 3 h
  2. customis removed in vacuo

Sources & evidence

ORD record
ord-619416d3517c4900a8924767d1127d46
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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