Ammonium Chloride → 3-Fluoro-4-(6-(2-morpholinopyridin-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamine

HRID 347575Notes

Reaction equation

HRID 347575 reaction equation
[F:1][C:2]1[CH:29]=[C:28]([N+:30]([O-])=O)[CH:27]=[CH:26][C:3]=1[O:4][C:5]1[C:10]2=[CH:11][C:12]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH:15]=3)=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1.[NH4+].[Cl-]>C1COCC1.CO.[Zn]>[F:1][C:2]1[CH:29]=[C:28]([NH2:30])[CH:27]=[CH:26][C:3]=1[O:4][C:5]1[C:10]2=[CH:11][C:12]([C:14]3[CH:19]=[CH:18][N:17]=[C:16]([N:20]4[CH2:21][CH2:22][O:23][CH2:24][CH2:25]4)[CH:15]=3)=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 210816524-(2-Fluoro-4-nitrophenoxy)-6-(2-morpholinopyridin-4-yl)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 210816163-Fluoro-4-(6-(2-morpholinopyridin-4-yl)pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamineYield 82%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(2-fluoro-4-nitrophenoxy)-6-(2-morpholinopyridin-4-yl)pyrrolo[2,1-f][1,2,4]triazine (54 mg, 0.12 mmol) in a mixture of THF (2.0 mL) and MeOH (2.0 mL) were added NH4Cl (127 mg, 2.4 mmol) and Zn dust (78 mg, 1.2 mmol). The reaction mixture was stirred at room temperature for 3 h, filtered and concentrated in vacuo. The residue was purified by preparative HPLC to provide the desired product (40 mg, 82% yield). MS(ESI) m/z 407.19 (M+H)+.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-89b9600da87a4343af6ef320219054ec
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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