Acetic Anhydride → HCID 178476597, compound

HRID 245764Notes

Reaction equation

HRID 245764 reaction equation
[Cl:1][C:2]1[C:3]([CH2:8][NH:9][C:10]([C@H:12]2[CH2:17][CH2:16][C@@H:15]([OH:18])[CH2:14][CH2:13]2)=[O:11])=[N:4][CH:5]=[CH:6][N:7]=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:19]([O:18][C@H:15]1[CH2:16][CH2:17][C@@H:12]([C:10](=[O:11])[NH:9][CH2:8][C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[CH:5][N:4]=2)[CH2:13][CH2:14]1)(=[O:21])[CH3:20]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 178523098HCID 178523098, compound

Product 1

HCID 178476597HCID 178476597, compoundYield 92.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To (cis)-N-((3-chloropyrazin-2-yl)methyl)-4-hydroxycyclohexanecarboxamide (57.4 mmol, 15.47 g) and 4-dimethylaminopyridine (5.74 mmol, 0.701 g) in pyridine (125 ml) at 0° C. was added dropwise acetic anhydride (60.2 mmol, 5.69 ml) and the mixture was stirred at room temperature for one hour. Then the reaction was quenched with 4 N hydrochloric acid to a pH of four and extracted with ethyl acetate three times. The combined organic layers were dried (MgSO4) and concentrated in vacuo. The residue was taken up in toluene and concentrated in vacuo again. The residue was dissolved in dichloromethane (100 ml) and washed with 1 M hydrochloric acid (100 ml). The organic layer was washed with brine, dried (MgSO4) and concentrated in vacuo to give (cis)-4-((3-chloropyrazin-2-yl)methylcarbamoyl)cyclohexyl acetate (16.5 g)

Workup

  1. customThen the reaction was quenched with 4 N hydrochloric acid to a pH of four
  2. extractionextracted with ethyl acetate three times
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. concentrationconcentrated in vacuo again
  6. dissolutionThe residue was dissolved in dichloromethane (100 ml)
  7. washwashed with 1 M hydrochloric acid (100 ml)
  8. washThe organic layer was washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8341666057b442f7ad4556243044767d
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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