8-Bromooctanamide → (7-Carbamoyl-heptyl)-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide

HRID 882911Notes

Reaction equation

HRID 882911 reaction equation
[CH3:1][N:2]([CH3:17])[CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:13]([NH2:14])=[N:12][C:11]([NH2:15])=[C:10]([Cl:16])[N:9]=1)=[O:7].[Br:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([NH2:28])=[O:27]>CN(C=O)C>[Br-:18].[C:26]([CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][N+:2]([CH2:3][CH2:4][NH:5][C:6]([C:8]1[C:13]([NH2:14])=[N:12][C:11]([NH2:15])=[C:10]([Cl:16])[N:9]=1)=[O:7])([CH3:17])[CH3:1])(=[O:27])[NH2:28]

Participants

4

Reactant 2

HCID 131118468-Bromooctanamide2×HCID 151481303,5-Diamino-6-chloro-N-[2-(dimethylamino)ethyl]-2-pyrazinecarboxamide2×

Product 1

HCID 86656654(7-Carbamoyl-heptyl)-{2-[(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-dimethyl-ammonium bromide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid (2-dimethylamino-ethyl)-amide (Intermediate H) (100 mg, 0.39 mmol) and 8-Bromo-octanoic acid amide (Intermediate P) (130 mg, 0.6 mmol) in DMF (3 mL) is heated at 70° C. for 3 days. After this time, the solvent is removed in vacuo to yield an orange oil, which is triturated with acetone (2×10 mL) to afford the title compound. M+ 400.

Workup

  1. customAfter this time, the solvent is removed in vacuo
  2. customto yield an orange oil, which
  3. customis triturated with acetone (2×10 mL)

Sources & evidence

ORD record
ord-4067908afc0f42eaacf397e777483795
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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