(3-Fluoro-4-(5-methyl-6-(2-morpholinoethoxy)pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-N3-(4-fluorophenyl)malonamide, hydrochloride salt → 5-Chloropyrrolo[2,1-f][1,2,4]triazin-4(1H)-one

HRID 347517Notes

Reaction equation

HRID 347517 reaction equation
[ClH:1].FC1C=C(C(C(NC2C=CC(F)=CC=2)=O)C(N)=O)C=CC=1[O:9][C:10]1[C:15]2=[C:16](C)[C:17](OCCN3CCOCC3)=[CH:18][N:14]2[N:13]=[CH:12][N:11]=1>C(N)=O>[Cl:1][C:16]1[CH:17]=[CH:18][N:14]2[C:15]=1[C:10](=[O:9])[NH:11][CH:12]=[N:13]2

Participants

3

Reactant 1

HCID 131726240(3-Fluoro-4-(5-methyl-6-(2-morpholinoethoxy)pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-N3-(4-fluorophenyl)malonamide, hydrochloride salt2×

Product 1

HCID 1357420865-Chloropyrrolo[2,1-f][1,2,4]triazin-4(1H)-oneYield 67.2%

Reagents, catalysts & solvents 1

HCID 713FormamideSolvent

Procedure

A solution of methyl 1-amino-3-chloro-1H-pyrrole-2-carboxylate (10.0 g, 57.3 mmol, WO 03/099286: Compound A of Example 9) in formamide (40 mL) was heated at 170° C. for 1 h and then at 190° C. for 1 h. Upon cooling to room temperature, the mixture solidified. The product was purified by recrystallization from ethyl acetate to give the title compound (6.53 g, 67%) as a white solid. 1H NMR (CDCl3) δ 10.24 (br s, 1H), 7.48 (d, 1H, J=3.6 Hz), 7.29 (d, 1H, J=2.8 Hz), 6.47 (d, 1H, J=2.8 Hz); MS(ESI+) m/z 170.1 (M+H)+.

Workup

  1. customThe product was purified by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-86ab28101f004e829f685da9731a2551
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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