Ammonium Chloride → HCID 78161870, compound

HRID 521744Notes

Reaction equation

HRID 521744 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]1[CH:18]=[CH:17][C:16]([CH:19]([CH3:28])[CH2:20][NH:21][S:22]([CH:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])=[CH:15][CH:14]=1)[CH:8]=[CH:7]2)([O-])=O.[NH4+].[Cl-]>CO.[Zn]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([C:13]1[CH:14]=[CH:15][C:16]([CH:19]([CH3:28])[CH2:20][NH:21][S:22]([CH:25]([CH3:27])[CH3:26])(=[O:24])=[O:23])=[CH:17][CH:18]=1)[CH:8]=[CH:7]2

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 78161808HCID 78161808, compound

Product 1

HCID 78161870HCID 78161870, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of HJC-1-79 (120 mg, 0.3 mmol) in 4 mL of MeOH was added 4 mL of saturated NH4Cl (aq.). Zinc dust (195 mg, 3.0 mmol) was added into the solution at 0° C. The reaction was stirred at 0° C. for 0.5 h. TLC indicated that the starting material was gone. The mixture was partitioned between EtOAc (50 mL) and H2O (10 mL). The organic layer was separated and washed with brine (10 mL), dried over anhydrous Na2SO4, filtered and concentrated to give an oil residue. This residue was purified with silica gel column (Hexane/EtOAc=1/1) to obtain HJC-1-86 (70 mg, 63%) as a pale brown oil. 1H NMR (600 MHz, CDCl3) δ 7.43 (d, 2H, J=8.4 Hz), 7.37 (d, 1H, J=8.4 Hz), 7.32 (d, 2H, J=8.4 Hz), 7.24 (d, 1H, J=8.4 Hz), 6.96 (s, 1H), 6.68 (d, 1H, J=8.4 Hz), 6.49 (s, 1H), 4.29 (t, 1H, J=6.6 Hz), 3.34-3.40 (m, 2H), 3.25-3.30 (m, 2H), 3.06-3.10 (m, 1H), 3.00-3.05 (m, 1H), 1.35 (d, 3H, J=6.6 Hz), 1.32 (d, 3H, J=6.6 Hz), 1.28 (t, 3H, J=6.6 Hz). 13C NMR (150 MHz, CDCl3) δ 141.1, 140.2, 139.0, 130.8, 130.5, 128.5, 128.2, 124.2, 113.2, 111.2, 106.0, 102.7, 53.6, 50.5, 40.5, 19.2, 16.9, 16.6.

Workup

  1. customThe mixture was partitioned between EtOAc (50 mL) and H2O (10 mL)
  2. customThe organic layer was separated
  3. washwashed with brine (10 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oil residue
  8. customThis residue was purified with silica gel column (Hexane/EtOAc=1/1)

Sources & evidence

ORD record
ord-f910841c0ca54cdba5a9b819eaca3355
Source dataset
uspto-grants-2016_05
Patent number
US09328125B2

Reaction notes

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