Water → Ethyl ({5-[5-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)-2-methylphenoxy]pyridin-2-yl}carbamothioyl)carbamate

HRID 1874604Notes

Reaction equation

HRID 1874604 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[C:11]([NH:16][C:17](=[O:29])[C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([C:27]#[N:28])([CH3:26])[CH3:25])[CH:19]=3)[CH:12]=[CH:13][C:14]=2[CH3:15])=[CH:4][CH:3]=1.[C:30]([N:35]=[C:36]=[S:37])(=[O:34])[O:31][CH2:32][CH3:33].O>CS(C)=O>[C:27]([C:24]([C:20]1[CH:19]=[C:18]([C:17]([NH:16][C:11]2[CH:12]=[CH:13][C:14]([CH3:15])=[C:9]([CH:10]=2)[O:8][C:5]2[CH:4]=[CH:3][C:2]([NH:1][C:36]([NH:35][C:30](=[O:34])[O:31][CH2:32][CH3:33])=[S:37])=[N:7][CH:6]=2)=[O:29])[CH:23]=[CH:22][CH:21]=1)([CH3:26])[CH3:25])#[N:28]

Participants

5

Reactant 3

HCID 962WaterHCID 85320Ethyl isothiocyanatoformateHCID 68724247N-{3-[(6-aminopyridin-3-yl)oxy]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide

Product 1

HCID 86631986Ethyl ({5-[5-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)-2-methylphenoxy]pyridin-2-yl}carbamothioyl)carbamate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of N-{3-[(6-aminopyridin-3-yl)oxy]-4-methylphenyl}-3-(1-cyano-1-methylethyl)benzamide (4.71 g, 12.2 mmol) in dimethyl sulfoxide (100 mL) was added ethyl isothiocyanatocarbonate (1.73 mL, 14.6 mmol), and the mixture was stirred at room temperature for 6 hr. Water (300 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (200 mL, 50 mL). The combined organic layer was washed with saturated brine (50 mL) and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure to give ethyl ({5-[5-({[3-(1-cyano-1-methylethyl)phenyl]carbonyl}amino)-2-methylphenoxy]pyridin-2-yl}carbamothioyl)carbamate as a yellow amorphous solid. The obtained compound was used in the next reaction without further purification.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (200 mL, 50 mL)
  2. washThe combined organic layer was washed with saturated brine (50 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe insoluble material was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e50a9df4b68e4170a4ff5adcea1153fc
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

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