Diisopropylethylamine → cis-Methyl 2-(3-chloro-5-(n'-hydroxycarbamimidoyl)pyridin-2-ylamino)cyclopentanecarboxylate

HRID 1631041Notes

Reaction equation

HRID 1631041 reaction equation
[Cl:1][C:2]1[C:3]([NH:10][C@H:11]2[CH2:15][CH2:14][CH2:13][C@H:12]2[C:16]([O:18][CH3:19])=[O:17])=[N:4][CH:5]=[C:6]([C:8]#[N:9])[CH:7]=1.Cl.[NH2:21][OH:22].CCN(C(C)C)C(C)C>CCO>[Cl:1][C:2]1[C:3]([NH:10][C@H:11]2[CH2:15][CH2:14][CH2:13][C@H:12]2[C:16]([O:18][CH3:19])=[O:17])=[N:4][CH:5]=[C:6]([C:8](=[N:21][OH:22])[NH2:9])[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 443297Hydroxyamine hydrochlorideHCID 90293527HCID 90293527, compound

Product 1

HCID 90293497cis-Methyl 2-(3-chloro-5-(n'-hydroxycarbamimidoyl)pyridin-2-ylamino)cyclopentanecarboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of cis-methyl 2-(3-chloro-5-cyanopyridin-2-ylamino)cyclopentanecarboxylate (0.154 g; 0.55 mmol), hydroxylamine hydrochloride (0.057 g; 0.82 mmol) and DIEA (0.143 mL; 0.82 mmol) in EtOH (2 mL) was stirred at ambient temperature for 42 hours. The solvent was evaporated in vacuo and the residue dissolved in DCM/water. The mixture was passed through a hydrophobic frit and the solvent evaporated in vacuo to afford the title product (0.172 g; quantitative). 1H NMR (CDCl3, 400 MHz) δ 8.25 (1H, d, J=2 Hz), 7.74 (1H, d, J=2 Hz), 5.74 (1H, d, J=8.4 Hz), 4.77-4.70 (3H, m), 3.61 (3H, s), 3.19-3.14 (1H, m), 2.14-1.70 (6H, m).

Workup

  1. customThe solvent was evaporated in vacuo
  2. dissolutionthe residue dissolved in DCM/water
  3. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-3fdefb9764514174a7498df3835fe1e1
Source dataset
uspto-grants-2014_07
Patent number
US08791142B2

Reaction notes

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