1,1'-Carbonyldiimidazole → Imidazole-1-carboxylic acid (1-methanesulfonyl-piperidin-4-yl)-amide

HRID 909074Notes

Reaction equation

HRID 909074 reaction equation
FC(F)(F)C(O)=O.[CH3:8][S:9]([N:12]1[CH2:17][CH2:16][CH:15]([NH2:18])[CH2:14][CH2:13]1)(=[O:11])=[O:10].[C:19](N1C=CN=C1)([N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1)=[O:20]>CN(C)C=O>[CH3:8][S:9]([N:12]1[CH2:13][CH2:14][CH:15]([NH:18][C:19]([N:21]2[CH:25]=[CH:24][N:23]=[CH:22]2)=[O:20])[CH2:16][CH2:17]1)(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 11975076[1-(Methylsulfonyl)piperidin-4-yl]amine trifluoroacetate

Product 1

HCID 67095364Imidazole-1-carboxylic acid (1-methanesulfonyl-piperidin-4-yl)-amideYield 70.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 1-methanesulfonyl-piperidin-4-ylamine; compound with trifluoro-acetic acid (229.4 mg, 0.785 mmol, US20060014708) in N,N-dimethyl formamide (4.0 mL) was added TEA (101 mg, 1.004 mmol) and 1,1′-carbonyldiimidazole (Aldrich, 134 mg, 0.826 mmol). After it was stirred at rt for 2 hrs, the solvent was removed and the reaction mixture was extracted with EtOAc, and washed with water (2×), and saturated NaCl. The organic phase was separated, dried over Na2SO4, filtered and concentrated to give imidazole-1-carboxylic acid (1-methanesulfonyl-piperidin-4-yl)-amide (150.7 mg, 70.5%) which was used without further purification.

Workup

  1. customthe solvent was removed
  2. extractionthe reaction mixture was extracted with EtOAc
  3. washwashed with water (2×), and saturated NaCl
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e5deeabe936e41d6a4aa70de9967b414
Source dataset
uspto-grants-2011_09
Patent number
US08017607B2

Reaction notes

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