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Acetic Acid → (R)-5-(2-amino-2-oxo-1-phenylethylamino)-3-(quinolin-6-ylamino)pyrazine-2-carboxamide

HRID 2200478
Notes
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Reaction equation

HRID 2200478 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][C:6]([NH:20][C@H:21]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]([NH2:24])=[O:23])=[N:7][C:8]=1[NH:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][CH:14]=[CH:13]2)#[N:2].[OH-].[Na+].OO.CC(O)=[O:37]>CCO.CS(C)=O>[NH2:24][C:22](=[O:23])[C@H:21]([NH:20][C:6]1[N:7]=[C:8]([NH:9][C:10]2[CH:11]=[C:12]3[C:17](=[CH:18][CH:19]=2)[N:16]=[CH:15][CH:14]=[CH:13]3)[C:3]([C:1]([NH2:2])=[O:37])=[N:4][CH:5]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 86685594(R)-2-(5-cyano-6-(quinolin-6-ylamino)pyrazin-2-ylamino)-2-phenylacetamide

Product 1

HCID 86685595(R)-5-(2-amino-2-oxo-1-phenylethylamino)-3-(quinolin-6-ylamino)pyrazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 679
Dimethyl Sulfoxide
Solvent
HCID 702EthanolSolvent

Procedure

The compound (R)-2-(5-cyano-6-(quinolin-6-ylamino)pyrazin-2-ylamino)-2-phenylacetamide (15 mg, 0.037 mmol) was dissolved in EtOH (2 mL) and DMSO (1 mL), aq. 1N NaOH (1.0 mL) and aq. H2O2 (30%, 1.0 mL) were added. The mixture was stirred at room temperature for 20 min. HOAc (0.1 mL) was added. The mixture was then concentrated in vacuo. The residue was purified by HPLC to give the titled compound (9 mg). MS 414.3 (M+H); UV 201.1, 265.8, 297.2, 358.5 nm; t 0.445 min.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-40643158ec2041adbd5e67d79d8a184b
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09359308B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes