Ammonium Chloride → HCID 86708695, compound

HRID 1430976Notes

Reaction equation

HRID 1430976 reaction equation
[Cl-].[NH4+].[Cl:3][C:4]1[C:11]([N+:12]([O-])=O)=[CH:10][C:7]([C:8]#[N:9])=[CH:6][C:5]=1[O:15][CH:16]1[CH2:21][CH2:20][N:19]([C:22]2([CH3:26])[CH2:25][O:24][CH2:23]2)[CH2:18][CH2:17]1>CO.[Zn]>[NH2:12][C:11]1[CH:10]=[C:7]([CH:6]=[C:5]([O:15][CH:16]2[CH2:21][CH2:20][N:19]([C:22]3([CH3:26])[CH2:23][O:24][CH2:25]3)[CH2:18][CH2:17]2)[C:4]=1[Cl:3])[C:8]#[N:9]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 86708693HCID 86708693, compound

Product 1

HCID 86708695HCID 86708695, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Ammonium chloride (584 mg, 10.92 mmol) and zinc (356 mg, 5.46 mmol) were added to a solution of 4-chloro-3-((1-(3-methyloxetan-3-yl)piperidin-4-yl)oxy)-5-nitrobenzonitrile (96 mg, 0.273 mmol) in methanol (10 mL) and the reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered through celite and the filtrate was concentrated, the crude was purified by flash chromatography on silica gel using an automated ISCO system (loaded onto a 24 g dry column, 24 g column, eluting with 0-6% 2 N ammonia in methanol/dichloromethane). 3-amino-4-chloro-5-((1-(3-methyloxetan-3-yl)piperidin-4-yl)oxy)benzonitrile (87 mg) was obtained as a foaming solid.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated
  3. customthe crude was purified by flash chromatography on silica gel using an automated ISCO system (
  4. customdry column, 24 g column
  5. washeluting with 0-6% 2 N ammonia in methanol/dichloromethane)

Sources & evidence

ORD record
ord-5146ac9820704eda8ca9f6f2265c5e60
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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