Chloride → HCID 68431249, compound

HRID 1882024Notes

Reaction equation

HRID 1882024 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:22][C:23]([C:29]4[S:30][CH:31]=[CH:32][N:33]=4)=[CH:24][C:25]=3[C:26]([NH2:28])=O)[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[Cl-].O>CN(C)C=O>[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21]3[NH:22][C:23]([C:29]4[S:30][CH:31]=[CH:32][N:33]=4)=[CH:24][C:25]=3[C:26]#[N:28])[CH2:14][CH:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[CH:9][CH:8]=2)(=[O:5])=[O:6])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 312ChlorideHCID 962WaterHCID 59331303HCID 59331303, compound

Product 1

HCID 68431249HCID 68431249, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-{1-[4-(cyclopropylsulfonyl)phenyl]-2-(tetrahydro-2H-pyran-4-yl)ethyl}-5-(1,3-thiazol-2-yl)-1H-pyrrole-3-carboxamide (0.147 g) in N,N-dimethylformamide (5 mL) was added cyanuroyl chloride (0.061 g) under ice-cooling, m and the mixture was warmed to room temperature and stirred at room temperature for 16 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-70:30, volume ratio), and recrystallized from hexane-diethyl ether to give the title compound (0.093 g, yield 66%) as colorless crystals. MS: 468 (MH+). melting point 114-116° C.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed successively with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=30:70-70:30, volume ratio)
  7. customrecrystallized from hexane-diethyl ether

Sources & evidence

ORD record
ord-d4cfaf12ecf14c61be0599b3e16bdd05
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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