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

HRID 882920Notes

Reaction equation

HRID 882920 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH2:14][CH2:15][NH:16][C:17]([C:19]1[C:24]([NH2:25])=[N:23][C:22]([NH2:26])=[C:21]([Cl:27])[N:20]=1)=[O:18])[CH3:13])(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[NH2:7][CH2:8][CH2:9][CH2:10][CH2:11][N:12]([CH3:13])[CH2:14][CH2:15][NH:16][C:17]([C:19]1[C:24]([NH2:25])=[N:23][C:22]([NH2:26])=[C:21]([Cl:27])[N:20]=1)=[O:18]

Participants

4

Reactant 1

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

Product 1

HCID 866566603,5-Diamino-6-chloro-pyrazine-2-carboxylic acid {2-[(4-amino-butyl)-methyl-amino]-ethyl}-amide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

[4-({2-[(3,5-Diamino-6-chloro-pyrazine-2-carbonyl)-amino]-ethyl}-methyl-amino)-butyl]-carbamic acid tert-butyl ester (0.54 g, 2.2 mmol) in DCM (10 mL) and TFA (2 mL) is stirred at RT for 1 h. The solvent is removed in vacuo and the resulting oil is dissolved in saturated aqueous sodium carbonate solution. The mixture is concentrated in vacuo and the residue is dissolved in MeOH and filtered to remove the sodium carbonate. The filtrate is concentrated in vacuo to afford the title compound. [M+H]+ 316

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionthe resulting oil is dissolved in saturated aqueous sodium carbonate solution
  3. concentrationThe mixture is concentrated in vacuo
  4. dissolutionthe residue is dissolved in MeOH
  5. filtrationfiltered
  6. customto remove the sodium carbonate
  7. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-f1d63dc399aa439f98825655c603913a
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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