ChemicalBook CAS DataBase List 4-Chloro-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid methyl ester

4-Chloro-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid methyl ester synthesis

5synthesis methods

Product Name:4-Chloro-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid methyl ester
CAS Number:310442-40-1
Molecular formula:C9H8ClN3O2
Molecular Weight:225.63

310431-29-9 Synthesis

Methyl 5-methyl-4-oxo-1,4-dihydropyrrolo[2,1-f][1,2,4]triazine-6-carboxylate

310431-29-9
47 suppliers
$45.00/10mg

4-Chloro-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylic acid methyl ester

310442-40-1
22 suppliers
$504.32/5MG

Yield:310442-40-1 93%

Reaction Conditions:

with trichlorophosphate at 100; for 15 h;Product distribution / selectivity;

Steps:

27; 33 4-chloro-5-methyl-6-carbomethoxypyrrolo[2,1-f][1,2,4]triazine

Example 27 4-chloro-5-methyl-6-carbomethoxypyrrolo[2,1-f][1,2,4]triazine Phosphorous oxychloride (2.5 mL) was combined with Compound C of Example 19 (100 mg, 0.483 mmol) and heated at 100° C. overnight. The melt was allowed to cool to rt and dissolved in ethyl acetate. The mixture was neutralized with aqueous NaHCO₃ and extracted twice with ethyl acetate. The combined organic washes were dried (Na₂SO₄) and concentrated to provide 101 mg (93%) of Example 27. MS: (M+H)⁺226.6 Example 33 5-Methyl-4-[[3-[(methylsulfonyl)amino]phenyl]amino]pyrrolo[2,1-f][1,2,4]triazine-6-carboxylic Acid Methyl EsterPhosphorus oxychloride was combined with Example 19 (30 mg, 0.14 mmol) and heated to 100° C. for 15 hrs. The melt was cooled and concentrated to remove excess reagent, then extracted with ethyl acetate (20 mL). The extract was washed with sat aqueous NaHCO₃, (10 mL) dried over MgSO₄and concentrated in vacuo to provide chlorinated compound Example 27. The residue was dissolved in DMF (2 mL) and 3(methylsulfonylamino)aniline (54 mg, 0.3 mmol) was added. The reaction mixture was stirred for 4 hrs under argon at 25° C. The crude reaction mixture was purified by preparative HPLC. The material obtained appeared to be a salt of the desired compound. The material was dissolved in ethyl acetate and washed with saturated aqueous NaHCO₃. Evaporation of the solvent gave 24 mg (40%) of Example 33. MS: [M+H]⁺=376.2; ¹H NMR (d-DMSO): δ 8.89 (s, 1H), 8.14 (s, 1H), 7.95 (s, 1H), 7.55 (s, 1H), 7.38 (s, 1H), 7.34-7.32 (m, 2H), 7.01 (d, J=8.0 Hz, 1H), 3.81 (s, 3H), 3.02 (s, 3H), 2.82 (s, 3H).

References:

US6982265,2006,B1 Location in patent:Page/Page column 38; 41

40318-15-8 Synthesis