Ethanol → HCID 57749095, compound

HRID 1874423Notes

Reaction equation

HRID 1874423 reaction equation
[CH3:1][N:2]1[C:6]([C:7]([NH:9][C:10]2[CH:11]=[C:12]([CH:29]=[CH:30][C:31]=2[F:32])[O:13][C:14]2[CH:15]=[CH:16][C:17]([NH:20][C:21]([NH:23]C(=O)OCC)=S)=[N:18][CH:19]=2)=[O:8])=[CH:5][C:4]([CH3:33])=[N:3]1.[Cl-].O[NH3+].C([N:40](CC)C(C)C)(C)C.C(O)C>O.CO>[NH2:23][C:21]1[N:20]=[C:17]2[CH:16]=[CH:15][C:14]([O:13][C:12]3[CH:29]=[CH:30][C:31]([F:32])=[C:10]([NH:9][C:7]([C:6]4[N:2]([CH3:1])[N:3]=[C:4]([CH3:33])[CH:5]=4)=[O:8])[CH:11]=3)=[CH:19][N:18]2[N:40]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 21645Hydroxylamine HClHCID 81531DiisopropylethylamineHCID 57749328HCID 57749328, compound

Product 1

HCID 57749095HCID 57749095, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of ethyl ({[5-(3-{[(1,3-dimethyl-1H-pyrazol-5-yl) carbonyl]amino}-4-fluorophenoxy)pyridin-2-yl]amino}carbonothioyl)carbamate (1.15 g, 2.43 mmol), hydroxylammonium chloride (1.18 g, 17.0 mmol), N,N-diisopropylethylamine (2.12 mL, 12.2 mmol), ethanol (10 mL) and methanol (10 mL) was stirred at 80° C. for 8 hr. The reaction mixture was diluted with water and extracted with ethyl acetate (×3). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was collected by filtration and washed with ethyl acetate-hexane to give the title compound (650 mg, 70%) as a yellow solid.

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. filtrationthe residue was collected by filtration
  7. washwashed with ethyl acetate-hexane

Sources & evidence

ORD record
ord-dfb65ee2f2e34f1fbbdd1ebd31f3a32f
Source dataset
uspto-grants-2012_11
Patent number
US08304557B2

Reaction notes

Loading…