Benzyl bromoacetate → HCID 178512395, compound

HRID 77516Notes

Reaction equation

HRID 77516 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10]([NH:12][C:13]([C:15]1[C:20]([NH2:21])=[N:19][C:18]([NH2:22])=[C:17]([Cl:23])[N:16]=1)=[O:14])=[NH:11])[CH2:2]2.[Br:24][CH2:25][C:26]([O:28]CC1C=CC=CC=1)=[O:27]>CN(C=O)C>[Br-:24].[C:26]([CH2:25][N+:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([NH:9][C:10]([NH2:11])=[N:12][C:13]([C:15]1[C:20]([NH2:21])=[N:19][C:18]([NH2:22])=[C:17]([Cl:23])[N:16]=1)=[O:14])[CH2:2]2)([OH:28])=[O:27]

Participants

4

Reactant 2

HCID 62576Benzyl bromoacetateHCID 178512394HCID 178512394, compound2×

Product 1

HCID 178512395HCID 178512395, compoundYield 16%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(1-Aza-bicyclo[2.2.2]oct-3-yl)-N′-(3,5-diamino-6-chloro-pyrazine-2-carbonyl)-guanidine (Intermediate 4, 152 mg, content ca. 66%, 0.30 mmol) and benzyl bromoacetate (Aldrich, 0.052 mL, 0.33 mmol) are treated with DMF (1 mL) and the mixture stirred at r.t. for ca. 18 h. The crude mixture is purified by preparative HPLC (5 mM ammonium formate in H2O: CH3CN gradient) and further on a PoraPak Rxn RP cartridge (Waters, 6 mL), eluting with 0% to 100% acetonitrile in water. Drying under vacuum yields the title compound (23 mg).

Workup

  1. customThe crude mixture is purified by preparative HPLC (5 mM ammonium formate in H2O: CH3CN gradient) and further on a PoraPak Rxn RP cartridge (Waters, 6 mL)
  2. washeluting with 0% to 100% acetonitrile in water
  3. customDrying under vacuum

Sources & evidence

ORD record
ord-4e92d17ad73e48f7be100ee76dbd8ee7
Source dataset
uspto-grants-2014_09
Patent number
US08841309B2

Reaction notes

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