Tetrahydrofuran → HCID 59310146, compound

HRID 1513049Notes

Reaction equation

HRID 1513049 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][CH2:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N:22]1[C:26]2=[N:27][C:28](C(OCC)=O)=[CH:29][C:30]([CH3:31])=[C:25]2[NH:24][C:23]1=[O:37].[CH3:38][Mg]I.[Cl-].[NH4+].[O:43]1[CH2:47][CH2:46]CC1>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[CH2:15][CH2:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])=[CH:4][C:3]=1[N:22]1[C:26]2=[N:27][C:28]([C:47]([OH:43])([CH3:46])[CH3:38])=[CH:29][C:30]([CH3:31])=[C:25]2[NH:24][C:23]1=[O:37]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 25056523HCID 25056523, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 59310146HCID 59310146, compound

Procedure

To a solution of 3-[2-chloro-5-(2,3,4,5-tetrahydro-1H-1-benzoazepin-1-ylsulfonyl)-phenyl]-5-ethoxycarbonyl-7-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one (30 mg) in tetrahydrofuran (3 mL) was added methylmagnesium iodide (3 mol/L diethyl ether solution, 0.061 mL) under ice-cooling, and the mixture was stirred at room temperature overnight. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=2/3) to give the title compound (4 mg).

Workup

  1. temperaturecooling
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane−n-hexane/ethyl acetate=2/3)

Sources & evidence

ORD record
ord-3b174bd94fa044178b3432864a74c749
Source dataset
uspto-grants-2012_07
Patent number
US08217069B2

Reaction notes

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