Ammonium Acetate → 2-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-thiazole

HRID 1881964Notes

Reaction equation

HRID 1881964 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:32][CH:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)[C:14](=O)[CH2:15][CH2:16][C:17]([C:19]3[S:20][C:21]([CH:24]4[CH2:28][O:27][C:26]([CH3:30])([CH3:29])[O:25]4)=[CH:22][N:23]=3)=O)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C([O-])(=O)C.[NH4+:43]>C(O)(=O)C.C(OCC)(=O)C>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([C:14]3[NH:43][C:17]([C:19]4[S:20][C:21]([CH:24]5[CH2:28][O:27][C:26]([CH3:29])([CH3:30])[O:25]5)=[CH:22][N:23]=4)=[CH:16][CH:15]=3)[CH2:32][CH:33]3[CH2:34][CH2:35][O:36][CH2:37][CH2:38]3)=[CH:11][CH:12]=2)(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 517165Ammonium AcetateHCID 593314965-[4-(cyclopropylsulfonyl)phenyl]-1-[5-(2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-thiazol-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

Product 1

HCID 593315412-(5-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-1H-pyrrol-2-yl)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-thiazoleYield 67%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 5-[4-(cyclopropylsulfonyl)phenyl]-1-[5-(2,2-dimethyl-1,3-dioxolan-4-yl)-1,3-thiazol-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione (730 mg) in acetic acid (15 mL) was added ammonium acetate (1.60 g), and the mixture was stirred at 110° C. for 45 min. 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 (470 mg, yield 67%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio). MS: 543 (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-8e4ff9b4be1c42debe7b71c45bd6f051
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

Loading…