Ammonium Acetate → 5-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-3-methyl-1H-pyrrol-2-yl)pyridine

HRID 1882012Notes

Reaction equation

HRID 1882012 reaction equation
[Si:1]([O:8][CH:9]([C:11]1[CH:12]=[CH:13][C:14]([C:17](=O)[CH:18]([CH3:42])[CH2:19][C:20](=O)[CH:21]([C:29]2[CH:34]=[CH:33][C:32]([S:35]([CH:38]3[CH2:40][CH2:39]3)(=[O:37])=[O:36])=[CH:31][CH:30]=2)[CH2:22][CH:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:15][CH:16]=1)[CH3:10])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+:48]>C(O)(=O)C.C(OCC)(=O)C>[Si:1]([O:8][CH:9]([C:11]1[CH:12]=[CH:13][C:14]([C:17]2[NH:48][C:20]([CH:21]([C:29]3[CH:34]=[CH:33][C:32]([S:35]([CH:38]4[CH2:40][CH2:39]4)(=[O:37])=[O:36])=[CH:31][CH:30]=3)[CH2:22][CH:23]3[CH2:24][CH2:25][O:26][CH2:27][CH2:28]3)=[CH:19][C:18]=2[CH3:42])=[N:15][CH:16]=1)[CH3:10])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 593312241-[5-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyridin-2-yl]-5-[4-(cyclopropylsulfonyl)phenyl]-2-methyl-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

Product 1

HCID 593315955-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-3-methyl-1H-pyrrol-2-yl)pyridineYield 74.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-[5-(1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyridin-2-yl]-5-[4-(cyclopropylsulfonyl)phenyl]-2-methyl-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione (180 mg) in acetic acid (5 mL) was added ammonium acetate (354 mg), and the mixture was stirred at 90° C. for 1 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (130 mg, yield 74%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS: 609 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c2fe33127fc0499fbff0adfd40cdfebb
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

Loading…