4-(2-fluoro-4-nitrophenoxy)-5-methyl-N-(2-morpholinoethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide → 4-(4-Amino-2-fluorophenoxy)-5-methyl-N-(2-morpholinoethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide

HRID 2117110Notes

Reaction equation

HRID 2117110 reaction equation
Cl.FC1C=C(NC(=O)CC(NC2C=CC(F)=CC=2)=O)C=CC=1OC1C2=C(C)C(OCCN3CCOCC3)=CN2N=CN=1.[F:43][C:44]1[CH:71]=[C:70]([N+:72]([O-])=O)[CH:69]=[CH:68][C:45]=1[O:46][C:47]1[C:52]2=[C:53]([CH3:67])[C:54]([C:56]([NH:58][CH2:59][CH2:60][N:61]3[CH2:66][CH2:65][O:64][CH2:63][CH2:62]3)=[O:57])=[CH:55][N:51]2[N:50]=[CH:49][N:48]=1>>[NH2:72][C:70]1[CH:69]=[CH:68][C:45]([O:46][C:47]2[C:52]3=[C:53]([CH3:67])[C:54]([C:56]([NH:58][CH2:59][CH2:60][N:61]4[CH2:66][CH2:65][O:64][CH2:63][CH2:62]4)=[O:57])=[CH:55][N:51]3[N:50]=[CH:49][N:48]=2)=[C:44]([F:43])[CH:71]=1

Participants

3

Reactant 2

HCID 210816454-(2-fluoro-4-nitrophenoxy)-5-methyl-N-(2-morpholinoethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamideHCID 131727132N1-(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 210816664-(4-Amino-2-fluorophenoxy)-5-methyl-N-(2-morpholinoethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamideYield 92.3%

Procedure

Following a procedure similar to that for the synthesis of Compound C of Example 36, 4-(2-fluoro-4-nitrophenoxy)-5-methyl-N-(2-morpholinoethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide (75 mg, 0.17 mmol) was converted to the title compound (65 mg, 92%). LCMS(ESI+) m/z 415.3 (M+H)+.

Sources & evidence

ORD record
ord-7777ec8916004158872c32a1ce40e988
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

Loading…