Ammonium Chloride → HCID 178478677, compound

HRID 2283614Notes

Reaction equation

HRID 2283614 reaction equation
C(OC(=O)[N:7]([S:13]([C:16]1[CH:21]=[C:20]([Cl:22])[C:19]([O:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][C:31]([F:34])([F:33])[F:32])=[CH:26][C:25]=2[C:35]2[C:36]([N+:46]([O-])=O)=[N:37][N:38](C3CCCCO3)[CH:39]=2)=[CH:18][C:17]=1[F:49])(=[O:15])=[O:14])[C:8]1[N:9]=[CH:10][S:11][CH:12]=1)(C)(C)C.[Cl-:51].[NH4+]>[Fe].C(O)C>[ClH:22].[ClH:51].[NH2:46][C:36]1[C:35]([C:25]2[CH:26]=[C:27]([O:30][C:31]([F:32])([F:33])[F:34])[CH:28]=[CH:29][C:24]=2[O:23][C:19]2[C:20]([Cl:22])=[CH:21][C:16]([S:13]([NH:7][C:8]3[N:9]=[CH:10][S:11][CH:12]=3)(=[O:14])=[O:15])=[C:17]([F:49])[CH:18]=2)=[CH:39][NH:38][N:37]=1

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 68047296tert-Butyl [(5-chloro-2-fluoro-4-{2-[3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]-4-(trifluoromethoxy)phenoxy}phenyl)sulfonyl]1,3-thiazol-4-ylcarbamate

Product 1

HCID 178478677HCID 178478677, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

tert-Butyl[(5-chloro-2-fluoro-4-{2-[3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl]-4-(trifluoromethoxy)phenoxy}phenyl)sulfonyl]1,3-thiazol-4-ylcarbamate (Preparation 25, 3.70 g, 4.84 mmol), and saturated aqueous ammonium chloride solution (17 mL) were added to ethanol (62 mL). A white precipitate formed. Iron (0.541 g, 9.68 mmol) was added and the reaction mixture heated at 80° C. After 2 hours the reaction mixture was cooled, filtered and concentrated in vacuo. The residue was slurried in water and the solid collected by filtration. The solid was rinsed with water, then dissolved in ethyl acetate, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was dissolved in a saturated solution of hydrogen chloride in methanol and heated at 50° C. for 2 hours. The solvent was removed in vacuo and the residue dissolved in a minimum amount of methanol. Ethyl acetate was added and the solution stirred for 4 hours while crystals formed. The solid was collected by filtration to afford the title compound as a white powder (1.75 g).

Workup

  1. customA white precipitate formed
  2. temperatureAfter 2 hours the reaction mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. filtrationthe solid collected by filtration
  6. washThe solid was rinsed with water
  7. dissolutiondissolved in ethyl acetate
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated in vacuo
  10. dissolutionThe residue was dissolved in a saturated solution of hydrogen chloride in methanol
  11. temperatureheated at 50° C. for 2 hours
  12. customThe solvent was removed in vacuo
  13. dissolutionthe residue dissolved in a minimum amount of methanol
  14. additionEthyl acetate was added
  15. customformed
  16. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-d7709198eeab4c19bea73541b1090114
Source dataset
uspto-grants-2015_09
Patent number
US09145407B2

Reaction notes

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