3-Fluoro-4-(5-methyl-6-(2-(4-methylpiperazin-1-yl)ethoxy)pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamine → N1-(3-Fluoro-4-(5-methyl-6-(2-(4-methylpiperazin-1-yl)ethoxy)pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-N3-(4-fluorophenyl)malonamide, bis-hydrochloride salt

HRID 347503Notes

Reaction equation

HRID 347503 reaction equation
[ClH:1].FC1C=C([CH:29]([C:33]([NH:35][C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)=[O:34])[C:30](N)=[O:31])C=CC=1OC1C2=C(C)C(OCCN3CCOCC3)=CN2N=CN=1.[F:43][C:44]1[CH:45]=[C:46]([NH2:71])[CH:47]=[CH:48][C:49]=1[O:50][C:51]1[C:56]2=[C:57]([CH3:70])[C:58]([O:60][CH2:61][CH2:62][N:63]3[CH2:68][CH2:67][N:66]([CH3:69])[CH2:65][CH2:64]3)=[CH:59][N:55]2[N:54]=[CH:53][N:52]=1>>[ClH:1].[ClH:1].[F:43][C:44]1[CH:45]=[C:46]([NH:71][C:30](=[O:31])[CH2:29][C:33]([NH:35][C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)=[O:34])[CH:47]=[CH:48][C:49]=1[O:50][C:51]1[C:56]2=[C:57]([CH3:70])[C:58]([O:60][CH2:61][CH2:62][N:63]3[CH2:64][CH2:65][N:66]([CH3:69])[CH2:67][CH2:68]3)=[CH:59][N:55]2[N:54]=[CH:53][N:52]=1

Participants

3

Reactant 2

HCID 210816093-Fluoro-4-(5-methyl-6-(2-(4-methylpiperazin-1-yl)ethoxy)pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamineHCID 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 131726241N1-(3-Fluoro-4-(5-methyl-6-(2-(4-methylpiperazin-1-yl)ethoxy)pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)-N3-(4-fluorophenyl)malonamide, bis-hydrochloride saltYield 46%

Procedure

Following a procedure similar to that for the synthesis of Compound D of Example 36, 3-fluoro-4-(5-methyl-6-(2-(4-methylpiperazin-1-yl)ethoxy)pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)benzenamine (60 mg, 0.15 mmol) was converted the title compound (30 mg, 46%) as a 2.HCl salt. 1H NMR (DMSO-d6) δ 10.63 (s, 1H), 10.37 (s, 1H), 8.04 (s, 1H), 7.99 (s, 1H), 7.80 (d, 1H), 7.61 (m, 2H), 7.40 (m, 2H), 7.16 (m, 2H), 4.42 (br s, 2H), 3.38-3.60 (m, 10H), 2.81 (s, 3H), 2.40 (s, 3H);). MS(ESI+) m/z 580.3 (M+H)+.

Sources & evidence

ORD record
ord-47128cb2c5b0481eb2b9e47ec7d696ef
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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