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

HRID 347502Notes

Reaction equation

HRID 347502 reaction equation
Cl.FC1C=C(C(C(NC2C=CC(F)=CC=2)=O)C(N)=O)C=CC=1OC1C2=C(C)C(OCCN3CCOCC3)=CN2N=CN=1.[F:43][C:44]1[CH:70]=[C:69]([N+:71]([O-])=O)[CH:68]=[CH:67][C:45]=1[O:46][C:47]1[C:52]2=[C:53]([CH3:66])[C:54]([O:56][CH2:57][CH2:58][N:59]3[CH2:64][CH2:63][N:62]([CH3:65])[CH2:61][CH2:60]3)=[CH:55][N:51]2[N:50]=[CH:49][N:48]=1>>[F:43][C:44]1[CH:70]=[C:69]([NH2:71])[CH:68]=[CH:67][C:45]=1[O:46][C:47]1[C:52]2=[C:53]([CH3:66])[C:54]([O:56][CH2:57][CH2:58][N:59]3[CH2:60][CH2:61][N:62]([CH3:65])[CH2:63][CH2:64]3)=[CH:55][N:51]2[N:50]=[CH:49][N:48]=1

Participants

3

Reactant 2

HCID 210816414-(2-Fluoro-4-nitrophenoxy)-5-methyl-6-(2-(4-methylpiperazin-1-yl)-ethoxy)pyrrolo[2,1-f][1,2,4]triazineHCID 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 salt

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 51.1%

Procedure

Following a procedure similar to that for the synthesis of Compound C of Example 36, 4-(2-fluoro-4-nitrophenoxy)-5-methyl-6-(2-(4-methylpiperazin-1-yl)ethoxy)pyrrolo[2,1-f][1,2,4]triazine (2.90 g, 6.74 mmol) was converted to the title compound (1.38 g, 51%). MS(ESI+) m/z 401.3 (M+H)+.

Sources & evidence

ORD record
ord-219e2e8ee0e7477785c18cf19e3f129e
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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