Acetic Acid → HCID 136335113, compound

HRID 226498Notes

Reaction equation

HRID 226498 reaction equation
[C:1]([OH:4])(=[O:3])[CH3:2].[OH:5][NH:6][C:7](=[O:30])/[CH:8]=[CH:9]/[C:10]1[CH:15]=[N:14][C:13]([NH:16][C@@H:17]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:18]2)=[CH:12][N:11]=1.CCOC(C)=O>C(#N)C.C1COCC1>[C:1]([OH:4])(=[O:3])[CH3:2].[OH:5][NH:6][C:7](=[O:30])/[CH:8]=[CH:9]/[C:10]1[CH:15]=[N:14][C:13]([NH:16][C@@H:17]2[CH2:21][CH2:20][N:19]([CH2:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:18]2)=[CH:12][N:11]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 8857Ethyl AcetateHCID 136152675HCID 136152675, compound

Product 1

HCID 136335113HCID 136335113, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of acetic acid (3.2 μL) in acetonitrile (29.2 μL) was added to the mixture of (2E)-N-hydroxy-3-(5-{[(3R)-1-(2-phenylethyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylamide (20 mg) in THF (0.1 mL) and acetonitrile (0.1 mL) and the mixture was stirred at ambient temperature for 5 minutes. To the mixture was added AcOEt (1.5 mL) and isolated precipitate was collected by filtration to give (2E)-N-hydroxy-3-(5-{[(3R)-1-(2-phenylethyl)-3-pyrrolidinyl]amino}-2-pyrazinyl)acrylamide acetate (18 mg).

Workup

  1. customisolated precipitate
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-258675223ca2463992233f296cbb8d2c
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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