Acetamidine monohydrochloride → HCID 136353895, compound

HRID 2243215Notes

Reaction equation

HRID 2243215 reaction equation
[C:1]([C:3]1([C:9]2[CH:10]=[C:11]([S:15][C:16]3[CH:21]=[CH:20][C:19]([NH:22][C:23](NN)=[O:24])=[CH:18][CH:17]=3)[CH:12]=[CH:13][CH:14]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)#[N:2].Cl.[C:28]([NH2:31])(=[NH:30])[CH3:29]>>[CH3:29][C:28]1[NH:31][C:23](=[O:24])[N:22]([C:19]2[CH:20]=[CH:21][C:16]([S:15][C:11]3[CH:10]=[C:9]([C:3]4([C:1]#[N:2])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]4)[CH:14]=[CH:13][CH:12]=3)=[CH:17][CH:18]=2)[N:30]=1

Participants

3

Reactant 2

HCID 67170Acetamidine monohydrochlorideHCID 68692078HCID 68692078, compound

Product 1

HCID 136353895HCID 136353895, compound

Conditions

Temperature
120 °C

Procedure

A mixture of N-(4-{[3-(4-cyanotetrahydro-2H-pyran-4-yl)phenyl]thio}phenyl) hydrazinecarboxamide (1.0 g, 2.72 mmol) (example 6) and acetamidine hydrochloride (1.16 g, 12.22 mmol) was evacuated for about 15 minutes. Dry dimethylformamide (10 mL) was added under nitrogen atmosphere and the mixture was heated at about 120° C. for about 7-8 hours. The solvent was evaporated under vacuum and a saturated solution of potassium carbonate was added until the mixture became basic. The resulting mixture was extracted with ethyl acetate, washed with water, dried over anhydrous sodium sulphate, filtered and the solvent evaporated under vacuum to afford a colorless oily residue, which was purified by column chromatography over silica gel using ethyl acetate and hexane (4:1) to yield the title product as a white fluffy solid. Yield: 0.500 g.

Workup

  1. customwas evacuated for about 15 minutes
  2. additionDry dimethylformamide (10 mL) was added under nitrogen atmosphere
  3. customThe solvent was evaporated under vacuum
  4. additiona saturated solution of potassium carbonate was added until the mixture
  5. extractionThe resulting mixture was extracted with ethyl acetate
  6. washwashed with water
  7. dry with materialdried over anhydrous sodium sulphate
  8. filtrationfiltered
  9. customthe solvent evaporated under vacuum
  10. customto afford a colorless oily residue, which
  11. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-3dca2e3cbe264da58447316c6840c0e3
Source dataset
uspto-grants-2010_03
Patent number
US07674811B2

Reaction notes

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