Sodium Hydroxide → 3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid {(S)-2-[3-(4-methoxy-phenyl)-propylamino]-pentyl}-amide hydrochloride

HRID 882906Notes

Reaction equation

HRID 882906 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:17][CH2:18][CH3:19])[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].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH:30]=O)=[CH:24][CH:23]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(Cl)Cl>[ClH:16].[CH3:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][CH2:30][NH:2][C@@H:3]([CH2:17][CH2:18][CH3:19])[CH2:4][NH:5][C:6]([C:8]2[C:13]([NH2:14])=[N:12][C:11]([NH2:15])=[C:10]([Cl:16])[N:9]=2)=[O:7])=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 111266073-(4-Methoxyphenyl)propanalHCID 866518883,5-Diamino-6-chloro-pyrazine-2-carboxylic acid ((S)-2-amino-pentyl)-amide hydrochloride

Product 1

HCID 866518933,5-Diamino-6-chloro-pyrazine-2-carboxylic acid {(S)-2-[3-(4-methoxy-phenyl)-propylamino]-pentyl}-amide hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid ((S)-2-amino-pentyl)-amide hydrochloride (400 mg, 1.467 mmol), 3-(4-methoxyphenyl)propionaldehyde (181 mg, 1.103 mmol) and sodium triacetoxyborohydride (467 mg, 2.205 mmol) are dissolved in DCM (150 mL). The reaction mixture is stirred at reflux overnight. To the reaction mixture is added 1 M NaOH solution (50 mL) and DCM (50 mL). The organic phase is separated and the aqueous phase is extracted once with DCM. The combined organic phases are washed with brine, dried (MgSO4), filtered and concentrated in vacuo to afford a yellow solid. Purification by flash column chromatography (SiO2, MeOH:DCM, gradient 2-10%+0.1% TEA) affords the title compound. [M+H]+ 421.

Workup

  1. temperatureat reflux overnight
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted once with DCM
  4. washThe combined organic phases are washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a yellow solid
  9. customPurification by flash column chromatography (SiO2, MeOH:DCM, gradient 2-10%+0.1% TEA)

Sources & evidence

ORD record
ord-1bf2418fc20749a1bc999820a33d0057
Source dataset
uspto-grants-2012_08
Patent number
US08236808B2

Reaction notes

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