Ammonium Chloride → HCID 67606149, compound

HRID 1024750Notes

Reaction equation

HRID 1024750 reaction equation
[C:1]([O:5][C:6](=[O:43])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:42])[C:16]2[CH:21]=[C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([N+:30]([O-])=O)[CH:25]=3)[CH:19]=[C:18]([O:33][C:34]3[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-]>C1COCC1.[Fe]>[C:1]([O:5][C:6](=[O:43])[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:42])[C:16]2[CH:17]=[C:18]([O:33][C:34]3[CH:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=3)[CH:19]=[C:20]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([NH2:30])[CH:25]=3)[CH:21]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 67606063HCID 67606063, compound

Product 1

HCID 67606149HCID 67606149, compoundYield 66%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.2 g (2.04 mmol) of {4-[3-(4-cyano phenoxy)-5-(3-nitro benzyloxy)benzoyl amino]cyclohexyl}carbamic acid tert-butyl ester, dissolved in 10 ml of THF, 0.455 g (8.16 mmol) of iron powder and 0.436 g (8.16 mmol) of NH4Cl solution (5 ml water) were mixed. The resulting reaction mixture was refluxed overnight. After completion of reaction, the reaction mixture was filtered through celite, and the filtrate was concentrated under reduced pressure. 100 ml water was added to the concentrated mixture and the mixture was extracted with 100 ml of ethyl acetate. The organic layer was washed with water followed by saturated brine, dried over anhydrous sodium sulphate and concentrated to afford crude compound which was purified by column chromatography using hexane-ethylacetate (10:2) to afford 0.75 g of the required product. 1H NMR (DMSO-d6): δ 1.25 (4H, m), 1.4 (9H, s), 1.8 (4H, m), 3.2 (1H, m), 3.7 (1H, m), 5.0 (2H, s), 5.15 (2H, s), 6.5 (2H, m), 6.62 (1H, s), 6.78 (1H, d), 6.94 (1H, s), 7.0 (1H, t), 7.12 (3H, m), 7.4 (1H, s), 7.82 (2H, d), 8.26 (1H, d).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed overnight
  3. customAfter completion of reaction
  4. filtrationthe reaction mixture was filtered through celite
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. addition100 ml water was added to the concentrated mixture
  7. extractionthe mixture was extracted with 100 ml of ethyl acetate
  8. washThe organic layer was washed with water
  9. dry with materialdried over anhydrous sodium sulphate
  10. concentrationconcentrated
  11. customto afford crude compound which
  12. customwas purified by column chromatography

Sources & evidence

ORD record
ord-82813e4bfe4345339436459d00888454
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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