Ammonium Chloride → HCID 178453964, compound

HRID 1024807Notes

Reaction equation

HRID 1024807 reaction equation
[C:1]([O:5][C:6](=[O:43])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14](=[O:42])[NH:15][C:16]2[CH:21]=[C:20]([O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=3)[CH:19]=[C:18]([O:31][C:32]3[CH:37]=[CH:36][C:35]([N+:38]([O-])=O)=[C:34]([NH2:41])[CH:33]=3)[CH:17]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>CO.[Zn]>[C:1]([O:5][C:6](=[O:43])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([C:14](=[O:42])[NH:15][C:16]2[CH:17]=[C:18]([O:31][C:32]3[CH:37]=[CH:36][C:35]([NH2:38])=[C:34]([NH2:41])[CH:33]=3)[CH:19]=[C:20]([O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=3)[CH:21]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 178453965HCID 178453965, compound

Product 1

HCID 178453964HCID 178453964, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

{Trans-4-[3-(3-amino-4-nitro-phenoxy)-5-(4-cyano-phenoxy)-phenyl-carbamoyl}-cyclohexyl]-carbamic acid tert-butyl ester (1.0 g, 1.7 mmol), zinc (1.11 g, 17.02 mmol) and ammoniumchloride (0.91 g, 17.02 mmol) were dissolved in 20 ml of methanol and stirred for 2 h at 60° C. After reaction completion contents were filtered through celite and filetrate was concentrated to afford 0.8 g of the required product. 1H NMR (DMSO-d6): δ 1.45 (9H, s), 1.78 (4H, m), 2.45 (4H, m), 3.2 (1H, m), 4.42 (2H, s), 6.45 (2H, m), 6.5 (1H, d), 6.71 (2H, m), 7.15 (2H, d), 7.3 (2H, s), 7.8 (2H, d), 8.28 (1H, d).

Workup

  1. customAfter reaction completion contents
  2. filtrationwere filtered through celite and filetrate
  3. concentrationwas concentrated

Sources & evidence

ORD record
ord-d12007f4d4ec40b39711f4733682d060
Source dataset
uspto-grants-2014_05
Patent number
US08722930B2

Reaction notes

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