Ethanol → 7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine-2-carboxylic acid amide hydrochloride

HRID 1262401Notes

Reaction equation

HRID 1262401 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]2[C:12]([CH:13]=[N:14][C:15]([C:18]#[N:19])=[N:16]2)=[CH:11][CH:10]=1.C([OH:22])C.[Cl:23][Si](C)(C)C.Cl.CCO.C(O[Si](C)(C)C)C>>[ClH:23].[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:17]2[C:12]([CH:13]=[N:14][C:15]([C:18]([NH2:19])=[O:22])=[N:16]2)=[CH:11][CH:10]=1

Participants

5

Reactant 4

HCID 702Ethanol2×HCID 6397ChlorotrimethylsilaneHCID 667124197-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine-2-carbonitrileHCID 131730671HCl EtOH EtOTMS

Product 1

HCID 667123627-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine-2-carboxylic acid amide hydrochlorideYield 68.4%

Procedure

7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine-2-carbonitrile (30.0 mg, 0.120 mmol) was suspended in Ethanol (3.0 mL, 51 mmol). Separately, Chlorotrimethylsilane (6.00 mL, 47.3 mmol) was added to Ethanol (9.00 mL, 154 mmol) in a vial, which was sealed and allowed to stand 20 min. The mixture of HCl/EtOH/EtOTMS was then added to the nitrile suspension. Monitoring by 1H-NMR (0.1 mL aliquots dried in vacuo) showed conversion overnight. Conc. in vacuo gave 7-(2-Methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazine-2-carboxylic acid amide hydrochloride (25 mg, 68%). 1H-NMR (DMSO-d6): 9.26 (s, 1H), 8.04 (s, 1H), 7.85 (s, 1H), 7.78 (d, 1H, J=7.8 Hz), 7.49 (m, 1H), 7.37 (s, 1H), 7.23 (m, 2H), 7.12 (m, 1H), 3.09 (s, 3H); LCMS (Bruker): 3.0 min, 269 (M+H).

Workup

  1. customwas sealed
  2. customMonitoring by 1H-NMR (0.1 mL aliquots dried in vacuo)
  3. customconversion overnight

Sources & evidence

ORD record
ord-8ebba6ae2aac48d5bfaa0a2226eee7db
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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