Water → HCID 59714987, compound

HRID 2223893Notes

Reaction equation

HRID 2223893 reaction equation
[C:1]([CH2:4][C:5]1([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([N:19]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][N:28]=3)[C:20]([C:22]3[O:23][CH:24]=[CH:25][CH:26]=3)=[O:21])[CH2:15][CH2:14]2)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)(=O)[NH2:2].C(N(CC)CC)C.CS(Cl)(=O)=O.O>ClCCl>[C:1]([CH2:4][C:5]1([CH2:11][CH2:12][N:13]2[CH2:18][CH2:17][CH:16]([N:19]([C:27]3[CH:32]=[CH:31][C:30]([CH3:33])=[CH:29][N:28]=3)[C:20]([C:22]3[O:23][CH:24]=[CH:25][CH:26]=3)=[O:21])[CH2:15][CH2:14]2)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)#[N:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471Triethylamine2×HCID 31297Methanesulfonyl chloride2×HCID 59714851HCID 59714851, compound

Product 1

HCID 59714987HCID 59714987, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[1-[2-[1-(carbamoylmethyl)cyclohexyl]ethyl]piperidin-4-yl]-N-(5-methylpyridin-2-yl)-2-furancarboxamide (154 mg) dissolved in dichloromethane (3 mL) was added triethylamine (0.10 mL). Methanesulfonyl chloride (0.038 mL) was added to the solution under ice cooling. After allowing the temperature to rise to room temperature, the solution was stirred for 24 hours. Triethylamine (0.14 mL) and methanesulfonyl chloride (0.063 mL) were further added to the solution under ice cooling. The solution was stirred at room temperature for 24 hours. Water was added to he solution and it was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The resulting residue was purified by chromatography (silica gel, chloroform:methanol=20:1) to give the title compound (133 mg).

Workup

  1. customto rise to room temperature
  2. stirringThe solution was stirred at room temperature for 24 hours
  3. extractionwas extracted with chloroform
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by chromatography (silica gel, chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-1269677fcdab411a9c5128610543b3bc
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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