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

HRID 1470765Notes

Reaction equation

HRID 1470765 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

5

Reactant 2

HCID 2794833N'-Hydroxy-2-methylpropanimidamideHCID 86666703HCID 86666703, compound

Product 1

HCID 67125514HCID 67125514, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 8857Ethyl AcetateSolvent

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.

Workup

  1. customAfter that the solvent is removed in vacuo and 15 mL ethanol and 2 mL conc. HCl solution
  2. additionare added
  3. temperatureThe mixture is refluxed for 3 h
  4. concentrationSubsequently the mixture is concentrated
  5. additionwater is added
  6. customthe precipitate is collected
  7. washwashed with water

Sources & evidence

ORD record
ord-0a5e82c0c18a4dacb690762dbbc03476
Source dataset
uspto-grants-2015_04
Patent number
US09006450B2

Reaction notes

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