Pyridine → HCID 69358377, compound

HRID 852577Notes

Reaction equation

HRID 852577 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][CH2:13][CH3:14])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].N1C=[CH:19][CH:18]=[CH:17][CH:16]=1.C([S:24](Cl)(=[O:26])=[O:25])C=C>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH2:16]([S:24]([NH:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([CH2:12][CH2:13][CH3:14])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:26])=[O:25])[CH2:17][CH:18]=[CH2:19]

Participants

7

Reactant 3

HCID 1049PyridineHCID 534496Prop-2-ene-1-sulfonyl chlorideHCID 45089280HCID 45089280, compound

Product 1

HCID 69358377HCID 69358377, compoundYield 32.4%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl 3-amino-5-propylbenzoate (D133) (2.49 g, 12.9 mmol, 1 equiv) in CH2Cl2 (25 ml) were added pyridine (1.13 ml, 14 mmol, 1.1 equiv), 2-propene-1-sulfonyl chloride (2 g, 12.9 mmol, 1 equiv) and DMAP (350 mg, 2.9 mmol, 0.2 equiv) and the resulting mixture was stirred at room temperature for 4 days. The solution was diluted with AcOEt and the organic phase was washed with H2O, dried over MgSO4 and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 4:1) gave methyl 3-[(3-buten-1-ylsulfonyl)amino]-5-propylbenzoate (D134) (1.3 g, 32%) as a colourless oil. [M−H]−=310.0, RT=3.39 min.

Workup

  1. washthe organic phase was washed with H2O
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by flash chromatography on silica gel (iso-hexane/AcOEt: 4:1)

Sources & evidence

ORD record
ord-2f0ae366e3b54bf1966aaf1bf390f2b1
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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