(Methoxycarbonylsulfamoyl)triethylammonium hydroxide → 5-[2-Pyridin-4-yl-5-(1,2,3,6-tetrahydro-pyridin-4-yl)-furan-3-yl]-indan-1-one oxime

HRID 271521Notes

Reaction equation

HRID 271521 reaction equation
O[C:2]1([C:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[C:10]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[C:24](=[N:28][OH:29])[CH2:23][CH2:22]4)[CH:9]=2)[CH2:7][CH2:6][NH:5][CH2:4][CH2:3]1.[OH-].COC(NS([N+](CC)(CC)CC)(=O)=O)=O>C1COCC1.C(OCC)(=O)C.O>[N:16]1[CH:17]=[CH:18][C:13]([C:11]2[O:12][C:8]([C:2]3[CH2:7][CH2:6][NH:5][CH2:4][CH:3]=3)=[CH:9][C:10]=2[C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[C:24](=[N:28][OH:29])[CH2:23][CH2:22]3)=[CH:14][CH:15]=1

Participants

6

Reactant 2

HCID 11032497(Methoxycarbonylsulfamoyl)triethylammonium hydroxideHCID 1363552515-[5-(4-Hydroxy-piperidin-4-yl)-2-pyridin-4-yl-furan-3-yl]-indan-1-one oxime

Product 1

HCID 1363552525-[2-Pyridin-4-yl-5-(1,2,3,6-tetrahydro-pyridin-4-yl)-furan-3-yl]-indan-1-one oximeYield 60.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the product of Example 29, Step 1 (1.06 g, 2.0 mmol) in THF (25 ml) at 0° C. was treated with (methoxycarbonylsulfamoyl)-triethylammonium hydroxide inner salt (Burgess reagent, 952 mg, 4 mmol). After 18 hours at room temperature the mixture was diluted with ethyl acetate and water. The organic phase was washed with water and brine, dried and concentrated in vacuo. Purification of the residue by silica gel chromatography gave the title compound (450 mg, 46%); MS(ES+) m/e 486 [M+H]+.

Workup

  1. washThe organic phase was washed with water and brine
  2. customdried
  3. concentrationconcentrated in vacuo
  4. customPurification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-1949900c95ff40e99c4c6963f76343fb
Source dataset
uspto-grants-2008_11
Patent number
US07452906B2

Reaction notes

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