Ammonium Chloride → HCID 72192936, compound

HRID 1404833Notes

Reaction equation

HRID 1404833 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:5]=[C:4]([N+:17]([O-])=O)[C:3]=1[NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24].[Cl-].[NH4+]>CO.O.[Zn]>[NH2:17][C:4]1[CH:5]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:7]=[C:2]([F:1])[C:3]=1[NH:20][C:21](=[O:25])[O:22][CH2:23][CH3:24]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86700477Ethyl (2-fluoro-4-((4-fluorobenzyl)amino)-6-nitrophenyl)carbamate

Product 1

HCID 72192936HCID 72192936, compoundYield 71%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of compound 3 (0.075 g, 0.24 mmol, 1.0 equiv) in methanol (3 mL) was added zinc powder (0.0800 g, 1.22 mmol, 5.00 equiv) followed by ammonium chloride solution (0.065 g, 1.2 mmol, 5.0 equiv) in water (1 mL). The reaction mixture was stirred at RT for 4 h. After consumption of the starting material (by TLC), the reaction mixture was diluted with DCM (10 mL), water (10 mL) and filtered through a pad of celite. The organic layer was separated from filtrate and the aqueous layer was extracted with DCM (2×10 mL). The combined organic extracts were dried over anhydrous Na2SO4, concentrated under vacuum to give crude; which was purified by silica gel column chromatography (EtOAc/Hexane, 1:4) to afford compound 2A (0.050 g, 71%) as an off-white solid. TLC: 40% EtOAc/Hexane (Rf: 0.20); 1H NMR (400 MHz, CDCl3): δ 7.32-7.29 (m, 2H), 7.04 (t, J=8.8 Hz, 2H), 5.84 (d, J=9.6 Hz, 1H), 5.78 (s, 1H), 4.25-4.18 (m, 4H), 4.04-3.96 (m, 3H), 1.30 (t, J=6.8 Hz, 3H); LC-MS: m/z=322 (M++1) at RT 3.38 (99.0% purity); UPLC purity: 99.5%.

Workup

  1. customAfter consumption of the starting material (by TLC)
  2. additionthe reaction mixture was diluted with DCM (10 mL), water (10 mL)
  3. filtrationfiltered through a pad of celite
  4. customThe organic layer was separated from filtrate
  5. extractionthe aqueous layer was extracted with DCM (2×10 mL)
  6. dry with materialThe combined organic extracts were dried over anhydrous Na2SO4
  7. concentrationconcentrated under vacuum
  8. customto give crude
  9. customwhich was purified by silica gel column chromatography (EtOAc/Hexane, 1:4)

Sources & evidence

ORD record
ord-95d8b0c810914bf88d1941e8747f0cb0
Source dataset
uspto-grants-2014_12
Patent number
US08916133B2

Reaction notes

Loading…