Hydrochloric Acid → N-(3-Fluoro-4-(5-methyl-6-(2-(4-methylpiperazin-1-yl)ethoxy)pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)nicotinamide, tris hydrochloride salt

HRID 2117108Notes

Reaction equation

HRID 2117108 reaction equation
[ClH:1].[F:2][C:3]1[CH:4]=[C:5]([NH:29][C:30](=[O:42])[CH2:31][C:32]([NH:34][C:35]2C=CC(F)=[CH:37][CH:36]=2)=O)[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:15]2=[C:16]([CH3:28])[C:17]([O:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26]O[CH2:24][CH2:23]3)=[CH:18][N:14]2[N:13]=[CH:12][N:11]=1.Cl.Cl.FC1C=C(NC(NC(=O)CC2C=CC(F)=CC=2)=S)C=CC=1O[C:53]1C2=C(C)C(OCCN3CCN(C)CC3)=CN2N=C[N:54]=1.Cl>>[ClH:1].[ClH:1].[ClH:1].[F:2][C:3]1[CH:4]=[C:5]([NH:29][C:30](=[O:42])[C:31]2[CH:37]=[CH:36][CH:35]=[N:34][CH:32]=2)[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:15]2=[C:16]([CH3:28])[C:17]([O:19][CH2:20][CH2:21][N:22]3[CH2:27][CH2:26][N:54]([CH3:53])[CH2:24][CH2:23]3)=[CH:18][N:14]2[N:13]=[CH:12][N:11]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 1317262361-(3-Fluoro-4-(5-methyl-6-(2-(4-methylpiperazin-1-yl)ethoxy)pyrrolo[2,1-f][1,2,4] triazin-4-yloxy)phenyl)-3-(2-(4-fluorophenyl)acetyl)thiourea, bis-hydrochloride salt2×HCID 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 131727133N-(3-Fluoro-4-(5-methyl-6-(2-(4-methylpiperazin-1-yl)ethoxy)pyrrolo[2,1-f][1,2,4]triazin-4-yloxy)phenyl)nicotinamide, tris hydrochloride salt

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 (20 mg, 0.05 mmol, Compound B of Example 45) was converted the tile compound (10 mg, 32%) as a 3.HCl salt. 1H NMR (CD3OD) δ 9.46 (s, 1H), 9.20 (d, 1H), 9.08 (d, 1H), 8.29 (m, 1H), 7.92 (d, 1H), 7.81 (s, 1H), 7.82 (s, 1H), 7.61 (m, 1H), 7.42 (m, 1H), 4.54 (m, 2H), 3.82-4.05 (m, 10H), 3.05 (s, 3H), 2.51 (s, 3H); MS(ESI+) m/z 506.2 (M+H)+.

Sources & evidence

ORD record
ord-146907061bce433dab7740d5838c1113
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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