Ammonium Chloride → 4-(4-Amino-2-fluorophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl ethylcarbamate

HRID 2114015Notes

Reaction equation

HRID 2114015 reaction equation
[CH2:1]([NH:3][C:4](=[O:27])[O:5][C:6]1[C:7]([CH3:26])=[C:8]2[N:13]([CH:14]=1)[N:12]=[CH:11][N:10]=[C:9]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([N+:22]([O-])=O)=[CH:18][C:17]=1[F:25])[CH3:2].[NH4+].[Cl-]>C(O)C.[Zn]>[CH2:1]([NH:3][C:4](=[O:27])[O:5][C:6]1[C:7]([CH3:26])=[C:8]2[N:13]([CH:14]=1)[N:12]=[CH:11][N:10]=[C:9]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][C:17]=1[F:25])[CH3:2]

Participants

5

Reactant 2

HCID 25517Ammonium ChlorideHCID 210816474-(2-Fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl ethylcarbamate

Product 1

HCID 210816674-(4-Amino-2-fluorophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl ethylcarbamateYield 70.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-(2-fluoro-4-nitrophenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazin-6-yl ethylcarbamate (12.5 mg, 0.033 mmol) in ethanol (2 mL) was added Zn (20 mg, 0.3 mmol) and NH4Cl (20 mg, 0.37 mmol). The reaction was stirred at room temperature for 1 h, filtered through Celite® and concentrated in vacuo to give the title compound (8 mg, 70%) as a white solid.

Workup

  1. filtrationfiltered through Celite®
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-af2d4e0f40b04cc1960c3ec74d32152e
Source dataset
uspto-grants-2008_10
Patent number
US07432373B2

Reaction notes

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