N'-Hydroxy-2-methylpropanimidamide → HCID 67125514, compound

Reaction equation

[C:1]([N:3]1[CH2:8][CH2:7][CH:6]([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]([NH:17][C:18](=[O:20])[CH3:19])[CH3:16])=[CH:11][CH:10]=2)[CH2:5][CH2:4]1)#[N:2].[OH:21][N:22]=[C:23](N)[CH:24]([CH3:26])[CH3:25]>C(OC(=O)C)C.[Cl-].[Zn+2].[Cl-]>[CH:24]([C:23]1[N:2]=[C:1]([N:3]2[CH2:8][CH2:7][CH:6]([C:9]3[CH:10]=[CH:11][C:12]([C@@H:15]([NH:17][C:18](=[O:20])[CH3:19])[CH3:16])=[CH:13][CH:14]=3)[CH2:5][CH2:4]2)[O:21][N:22]=1)([CH3:26])[CH3:25]

Participants

Procedure

0.9 mL (0.45 mmol) Zinc(II)chloride (0.5 M solution in THF) is added dropwise to a mixture of 40.7 mg (0.15 mmol) (S)—N-{1-[4-(1-cyano-piperidin-4-yl)-phenyl]-ethyl}-acetamide (XXVII.1) and 30.6 mg (0.30 mmol N′-hydroxy-2-methylpropanimidamide in 12 mL ethylacetate. The mixture is stirred for 12 h at rt. After that the solvent is removed in vacuo and 15 mL ethanol and 2 mL conc. HCl solution are added. The mixture is refluxed for 3 h. Subsequently the mixture is concentrated, water is added and the precipitate is collected and washed with water to yield the desired product.