Ammonium Chloride → 3-cyclopropyl-1-((2-methyloxazol-4-yl)methyl)-1H-indazol-4-amine

HRID 79463Notes

Reaction equation

HRID 79463 reaction equation
[CH:1]1([C:4]2[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][C:11]=3[N+:13]([O-])=O)[N:6]([CH2:16][C:17]3[N:18]=[C:19]([CH3:22])[O:20][CH:21]=3)[N:5]=2)[CH2:3][CH2:2]1.[Cl-].[NH4+]>CCO.O.ClCCl.[Fe]>[CH:1]1([C:4]2[C:12]3[C:11]([NH2:13])=[CH:10][CH:9]=[CH:8][C:7]=3[N:6]([CH2:16][C:17]3[N:18]=[C:19]([CH3:22])[O:20][CH:21]=3)[N:5]=2)[CH2:2][CH2:3]1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 672613544-((3-cyclopropyl-4-nitro-1H-indazol-1-yl)methyl)-2-methyloxazole

Product 1

HCID 672600223-cyclopropyl-1-((2-methyloxazol-4-yl)methyl)-1H-indazol-4-amineYield 76.8%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 6344DichloromethaneSolventHCID 19096565Water ethanolSolvent

Procedure

To a suspension of 4-((3-cyclopropyl-4-nitro-1H-indazol-1-yl)methyl)-2-methyloxazole (88 mg, 0.295 mmol) in EtOH/H2O (4:1; 2 mL) was added iron powder (0.33 g, 5.9 mmol) and ammonium chloride (15.8 mg, 0.295 mmol). The reaction mixture was heated at reflux for three hours. The reaction mixture was cooled to ambient temperature, diluted with excess dichloromethane, and the resulting suspension was dried over anhydrous sodium sulfate. The solids were removed by filtration and the filtrate was concentrated under reduced pressure. The crude product was dissolved in dichloromethane, passed through a silica plug, eluting with 10% MeOH/DCM, and concentrated to afford the product (60.8 mg) as a yellow oil.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for three hours
  3. dry with materialthe resulting suspension was dried over anhydrous sodium sulfate
  4. customThe solids were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe crude product was dissolved in dichloromethane
  7. washeluting with 10% MeOH/DCM
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a609097d36f346878efe52a81c1885ee
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

Loading…