Phenylacetyl chloride → HCID 178508789, compound

HRID 2365503Notes

Reaction equation

HRID 2365503 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]1[CH2:10][NH:9]/[C:8](=[N:11]\[C:12]([C:14]2[C:19]([NH2:20])=[N:18][C:17]([NH2:21])=[C:16]([Cl:22])[N:15]=2)=[O:13])/[NH:7]1.C(N(CC)CC)C.[C:30]1([CH2:36][C:37](Cl)=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CN(C=O)C>[C:30]1([CH2:36][C:37]([CH:2]([NH2:1])[CH2:3][CH2:4][CH2:5][C@H:6]2[CH2:10][NH:9]/[C:8](=[N:11]\[C:12]([C:14]3[C:19]([NH2:20])=[N:18][C:17]([NH2:21])=[C:16]([Cl:22])[N:15]=3)=[O:13])/[NH:7]2)=[O:38])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chloride2×HCID 8471TriethylamineHCID 178510993HCID 178510993, compound2×

Product 1

HCID 178508789HCID 178508789, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3,5-Diamino-6-chloro-pyrazine-2-carboxylic acid [(S)-4-(4-amino-butyl)-imidazolidin-(2E)-ylidene]-amide (Intermediate T) (0.032 g, 0.098 mmol) in DMF (1 ml) is added triethylamine (0.014 ml, 0.098 mmol) followed by phenylacetyl chloride (0.013 ml, 0.098 mmol). The suspension is stirred at room temperature for 90 minutes before a further 0.5 equivalents of phenylacetyl chloride (0.006 ml, 0.049 mmol) is added. The reaction is left to stir at room temperature for a further 18 hours. Purification by reverse phase chromatography (Isolute™ C18, 0-100% MeCN in water −0.1% TFA) followed by catch and release resin (SCX-2) eluting with MeOH and 7M NH3 in MeOH affords the title compound as an off-white solid; [M+H]+ 445.1

Workup

  1. additionis added
  2. waitThe reaction is left
  3. customPurification by reverse phase chromatography (Isolute™ C18, 0-100% MeCN in water −0.1% TFA)
  4. washeluting with MeOH and 7M NH3 in MeOH

Sources & evidence

ORD record
ord-abc31441cc2b4a70a2f0486b5d5dde08
Source dataset
uspto-grants-2014_04
Patent number
US08697687B2

Reaction notes

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