Water → HCID 22936609, compound

HRID 853523Notes

Reaction equation

HRID 853523 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]([O:6][C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][CH:15]=3)[CH:8]=2)=[CH:4][CH:3]=1.C1([O:30][C:31](=O)[NH:32][C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([S:39]([CH3:42])(=[O:41])=[O:40])[CH:34]=2)C=CC=CC=1.C(OCC)(=O)C.O>CS(C)=O>[CH3:42][S:39]([C:35]1[CH:34]=[C:33]([NH:32][C:31]([NH:1][C:2]2[CH:23]=[CH:22][C:5]([O:6][C:7]3[CH:8]=[C:9]([NH:13][C:14]4[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][CH:15]=4)[N:10]=[CH:11][N:12]=3)=[CH:4][CH:3]=2)=[O:30])[CH:38]=[CH:37][CH:36]=1)(=[O:40])=[O:41]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl Acetate2×HCID 22936234Phenyl 3-methylsulfonylphenylcarbamateHCID 22936907HCID 22936907, compound

Product 1

HCID 22936609HCID 22936609, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

N-(6-(4-Aminophenoxy)pyrimidin-4-yl)-4-methylsulfanylphenylamine (194 mg, 0.600 mmol) and (3-methylsulfonylphenyl)carbamic acid phenyl ester (192 mg, 0.660 mmol) were heated and stirred in dimethyl sulfoxide (2 ml) at 85° C. for 18 hours. The reaction solution was distributed between ethyl acetate and water, the organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. The obtained crude product was subjected to silica gel column chromatography (eluent—ethyl acetate), the fraction containing the target substance was concentrated and suspended in ethyl acetate, the suspension was diluted with hexane and the crystals were filtered out, washed with hexane and blow-dried to obtain the title compound (297 mg, 0.569 mmol, 95%) as colorless crystals.

Workup

  1. washthe organic layer was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthe drying agent was filtered off
  4. distillationthe filtrate was distilled off under reduced pressure
  5. customThe obtained crude product
  6. additionthe fraction containing the target substance
  7. concentrationwas concentrated
  8. additionthe suspension was diluted with hexane
  9. filtrationthe crystals were filtered out
  10. washwashed with hexane
  11. customblow-dried

Sources & evidence

ORD record
ord-6d86b122c910430ebf372e1ed2aa5f67
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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