Sodium Carbonate → HCID 67322286, compound

HRID 1846640Notes

Reaction equation

HRID 1846640 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:14]([NH:15][C:16](=[O:24])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)=[CH:13][C:12]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:11][N:10]=2)[CH2:5][CH2:4]1.C(=O)([O-])[O-].[Na+].[Na+].[C:35]1([CH2:41][S:42](Cl)(=[O:44])=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(#N)C.O>[CH2:41]([S:42]([NH:1][CH2:2][CH:3]1[CH2:4][CH2:5][N:6]([C:9]2[C:14]([NH:15][C:16](=[O:24])[C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[CH:18]=3)=[CH:13][C:12]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:11][N:10]=2)[CH2:7][CH2:8]1)(=[O:44])=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 74740Phenylmethanesulfonyl chlorideHCID 67342451HCID 67342451, compound

Product 1

HCID 67322286HCID 67322286, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To 0.028 g (0.066 mmol) of N-(4-aminomethyl-5′-methanesulfonyl-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-3′-yl)-3-chloro-benzamide in a mixture of acetonitrile (0.5 mL) and saturated aqueous sodium carbonate (0.5 mL) is added 0.015 mg (0.079 mmol) of phenylmethanesulfonyl chloride. The mixture is stirred overnight at room temperature then diluted with water and extracted with ethyl acetate. The combined organic phase is washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue is purified by preparative thin layer chromatography to give 0.027 g (72%) of the title compound (109) as a clear resin. [M+H]+=577.7.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phase is washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-5dacc8dacaf147b68371c138c010f3e3
Source dataset
uspto-grants-2015_02
Patent number
US08952004B2

Reaction notes

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