(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 → 4-(2-Fluoro-4-(nicotinamido)phenoxy)-5-methyl-N-(2-morpholinoethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide, bis-hydrochloride salt

HRID 347507Notes

Reaction equation

HRID 347507 reaction equation
[ClH:1].[F:2][C:3]1[CH:30]=[C:29]([NH:31][C:32](=[O:41])[C:33]2[CH:38]=[C:37](C)[CH:36]=C[C:34]=2F)[CH:28]=[CH:27][C:4]=1[O:5][C:6]1[C:11]2=[C:12]([CH3:26])[C:13]([C:15]([NH:17][CH2:18][CH2:19][N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)=[O:16])=[CH:14][N:10]2[N:9]=[CH:8][N:7]=1.Cl.FC1C=C(C(C(NC2C=CC(F)=CC=2)=O)C(N)=O)C=CC=1OC1C2=C(C)C(OCCN3CCOCC3)=CN2N=C[N:52]=1>>[ClH:1].[ClH:1].[F:2][C:3]1[CH:30]=[C:29]([NH:31][C:32](=[O:41])[C:33]2[CH:38]=[CH:37][CH:36]=[N:52][CH:34]=2)[CH:28]=[CH:27][C:4]=1[O:5][C:6]1[C:11]2=[C:12]([CH3:26])[C:13]([C:15]([NH:17][CH2:18][CH2:19][N:20]3[CH2:21][CH2:22][O:23][CH2:24][CH2:25]3)=[O:16])=[CH:14][N:10]2[N:9]=[CH:8][N:7]=1

Participants

3

Reactant 2

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×HCID 1317262434-(2-Fluoro-4-(2-fluoro-5-methylbenzamido)phenoxy)-5-methyl-N-(2-morpholinoethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide, hydrochloride salt

Product 1

HCID 1317262444-(2-Fluoro-4-(nicotinamido)phenoxy)-5-methyl-N-(2-morpholinoethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide, bis-hydrochloride saltYield 39%

Procedure

Following a procedure similar to that for the synthesis of Compound D of Example 50, 4-(4-amino-2-fluorophenoxy)-5-methyl-N-(2-morpholinoethyl)pyrrolo[2,1-f][1,2,4]triazine-6-carboxamide (30 mg, 0.07 mmol, Compound C of Example 50) was converted the title compound (16 mg, 39%) as a 2.HCl salt. 1H NMR (CD3OD) δ 9.08 (s, 1H), 8.70 (s, 1H), 8.44 (s, 1H), 8.17 (s, 1H), 7.87 (m, 2H), 7.38 (m, 2H), 7.22 (m, 2H), 3.82 (s, 4H), 3.61 (m, 2H), 2.75 (m, 9H); MS(ESI+) m/z 520.2 (M+H)+.

Sources & evidence

ORD record
ord-bcb12a1965304d1e884f1817363511ff
Source dataset
uspto-grants-2007_02
Patent number
US07173031B2

Reaction notes

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