Sodium Carbonate → [4-({2-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-methyl-amino)-butyl]-carbamic acid tert-butyl ester

HRID 882919Notes

Reaction equation

HRID 882919 reaction equation
[CH3:1][NH: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].[C:17]([NH:24][CH2:25][CH2:26][CH2:27][CH2:28]Br)([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C(=O)([O-])[O-].[Na+].[Na+]>CN(C=O)C>[C:20]([O:19][C:17](=[O:18])[NH:24][CH2:25][CH2:26][CH2:27][CH2:28][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])[CH3:1])([CH3:23])([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 10868765tert-butyl N-(4-bromobutyl)carbamateHCID 198618223,5-diamino-6-chloro-N-(2-methylaminoethyl)pyrazine-2-carboxamide2×

Product 1

HCID 86656659[4-({2-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-methyl-amino)-butyl]-carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture comprising 3,5-diamino-6-chloro-pyrazine-2-carboxylic acid (2-methylamino-ethyl)-amide (Intermediate E) (0.5 g, 2.0 mmol) and 4-(Boc-amino)butyl bromide (0.8 g, 3.1 mmol) in DMF (5 mL) is added sodium carbonate (0.4 g, 4.0 mmol). The resulting mixture is heated at reflux for 3 h and then allowed to cool to RT, filtered and concentrated in vacuo. The crude product is dissolved in DCM and filtered to remove any undissolved impurities. The filtrate is concentrated in vacuo to yield the title compound which is used in the next step without further purification.

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureat reflux for 3 h
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe crude product is dissolved in DCM
  6. filtrationfiltered
  7. customto remove any undissolved impurities
  8. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-82c095b8ca174f94b85ea27c8d891d9b
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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