Acetic Anhydride → HCID 178476598, compound

HRID 245669Notes

Reaction equation

HRID 245669 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 178523099HCID 178523099, compound

Product 1

HCID 178476598HCID 178476598, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

The total harvest of (trans)-N-((3-chloropyrazin-2-yl)methyl)-4-hydroxycyclohexanecarboxamide (10 mmol, 2.7 g) and 4-dimethylaminopyridine (1.0 mmol, 0.12 g) were dissolved in pyridine (25 ml), acetic anhydride (10.51 mmol, 0.994 ml) was added and the mixture was stirred at room temperature. After 1 hour the reaction was quenched in 185 mL of 2N hydrochloric acid (pH becomes four) and extracted with ethyl acetate three times. The combined organic layers were dried (sodium sulfate) and concentrated to give 2.8 g of (trans)-4-((3-chloropyrazin-2-yl)methylcarbamoyl)cyclohexyl acetate.

Workup

  1. customAfter 1 hour the reaction was quenched in 185 mL of 2N hydrochloric acid (pH becomes four)
  2. extractionextracted with ethyl acetate three times
  3. dry with materialThe combined organic layers were dried (sodium sulfate)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5cece22d18a6463aafc3e56c81e8f262
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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