Pyridine → HCID 69101039, compound

HRID 2114971Notes

Reaction equation

HRID 2114971 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([NH:8][C:9](=[O:25])[C:10]([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][CH2:13]2)=[O:11])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34].C(=O)([O-])O.[Na+]>ClCCl>[CH2:18]([CH:15]1[CH2:16][CH2:17][N:12]([C:10](=[O:11])[C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][S:33]([CH3:32])(=[O:35])=[O:34])[CH:3]=2)=[O:25])[CH2:13][CH2:14]1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 69100250HCID 69100250, compound

Product 1

HCID 69101039HCID 69101039, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 0.34 g (1 mmol) of N-(3-amino-phenyl)-2-(4-benzyl-piperidin-1-yl)-2-oxo-acetamide (Example 11) and 0.16 ml (2 mmol) of pyridine in 10 ml of dichloromethane 0.16 ml (2 mmol) of methanesulfonyl chloride in 2 ml of dichloromethane is added dropwise below 10° C., and the reaction mixture is stirred at room temperature for 10 hours. Then 50 ml of 8% sodium hydrogencarbonate solution is added to the mixture, the organic layer is separated and the water phase is extracted three times with 10 ml of dichloromethane. The combined organic layers are dried over sodium sulfate, concentrated, the residue is treated with diethylether and the crystals are filtered to yield 0.25 g (30%) of the title compound. Melting Point: 128-130° C. (diethylether)

Workup

  1. customthe organic layer is separated
  2. extractionthe water phase is extracted three times with 10 ml of dichloromethane
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. concentrationconcentrated
  5. additionthe residue is treated with diethylether
  6. filtrationthe crystals are filtered

Sources & evidence

ORD record
ord-0b359fd3015c440490a03206356f6de1
Source dataset
uspto-grants-2008_10
Patent number
US07435744B2

Reaction notes

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