Ethane, 2-bromo-1,1-diethoxy- → HCID 59331476, compound

HRID 1881955Notes

Reaction equation

HRID 1881955 reaction equation
[CH:1]1([CH2:6][CH:7]([C:18]2[NH:22][C:21]([C:23](=[S:25])[NH2:24])=[C:20]([CH3:26])[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:28][CH:29](OCC)OCC>CN(C)C(=O)C.C(OCC)(=O)C>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:22][C:21]([C:23]3[S:25][CH:28]=[CH:29][N:24]=3)=[C:20]([CH3:26])[CH:19]=2)[C:8]2[CH:9]=[CH:10][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:12][CH:13]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 59331536HCID 59331536, compound

Product 1

HCID 59331476HCID 59331476, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution (3 mL) of 5-{2-cyclopentyl-1-[4-(methylsulfonyl)phenyl]ethyl}-3-methyl-1H-pyrrole-2-carbothioamide (120 mg) in N,N-dimethylacetamide was added 2-bromo-1,1-diethoxyethane (125 mg), and the mixture was stirred at 60° C. for 2 hr, then at 100° C. for 4 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 brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (60 mg, yield 47%) was obtained as colorless amorphous crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). MS: 415 (MH+).

Workup

  1. waitat 100° C. for 4 hr
  2. temperatureAfter cooling to room temperature
  3. washwashed with water
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b73dad09c3f3452a9992d2d4f5a47a11
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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