Ammonium Chloride → 3-Fluoro-4-(5-methyl-6-(2-(4-methylpiperazin-1-yl)ethoxy)pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamine

HRID 1393939Notes

Reaction equation

HRID 1393939 reaction equation
[F:1][C:2]1[CH:28]=[C:27]([N+:29]([O-])=O)[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[C:10]2=[C:11]([CH3:24])[C:12]([O:14][CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][N:20]([CH3:23])[CH2:19][CH2:18]3)=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1.[Cl-].[NH4+]>CO.C1COCC1.[Zn]>[F:1][C:2]1[CH:28]=[C:27]([NH2:29])[CH:26]=[CH:25][C:3]=1[O:4][C:5]1[C:10]2=[C:11]([CH3:24])[C:12]([O:14][CH2:15][CH2:16][N:17]3[CH2:18][CH2:19][N:20]([CH3:23])[CH2:21][CH2:22]3)=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 210816414-(2-Fluoro-4-nitrophenoxy)-5-methyl-6-(2-(4-methylpiperazin-1-yl)-ethoxy)pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 210816093-Fluoro-4-(5-methyl-6-(2-(4-methylpiperazin-1-yl)ethoxy)pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamineYield 87%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-(2-fluoro-4-nitrophenoxy)-5-methyl-6-(2-(4-methylpiperazin-1-yl)ethoxy)pyrrolo[2,1-f][1,2,4]triazine (20 mg, 0.05 mmol) in anhydrous methanol (1 mL) and anhydrous THF (1 mL) at ambient temperature under nitrogen atmosphere was added zinc dust (33 mg, 50 mmol) and ammonium chloride (27 mg, 50 mmol). The reaction mixture was stirred for 7 h before the catalyst was filtered off and the filtrate was concentrated in vacuo to give a solid which was partitioned between chloroform and water. The aqueous phase was extracted twice with chloroform. The combined organic layers were washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo to give the desired compound (16 mg, 87%) as a solid. 1H NMR (CDCl3) δ 7.86-7.83 (m, 1H), 7.50-7.38 (m, 2H), 7.09-7.00 (m, 1H), 6.56-6.45 (m, 1H), 4.14 (t, 2H, J=5.5 Hz), 2.99-2.38 (m, 18H); MS(ESI+) m/z 401.4 (M+H)+.

Workup

  1. filtrationwas filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto give a solid which
  4. customwas partitioned between chloroform and water
  5. extractionThe aqueous phase was extracted twice with chloroform
  6. washThe combined organic layers were washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6571cac3e2e840079c4fc68443eba744
Source dataset
uspto-grants-2008_03
Patent number
US07348325B2

Reaction notes

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