1-(3-Aminopropyl)-4-methylpiperazine → HCID 44405398, compound

HRID 2113583Notes

Reaction equation

HRID 2113583 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][N:16]=[C:17](F)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:21]#[N:22])[CH:5]=[CH:6][C:7]=1[F:8].[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([CH2:30][CH2:31][CH2:32][NH2:33])[CH2:26][CH2:25]1>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][N:16]=[C:17]([NH:33][CH2:32][CH2:31][CH2:30][N:27]4[CH2:26][CH2:25][N:24]([CH3:23])[CH2:29][CH2:28]4)[CH:18]=3)[N:13]=[CH:12][C:11]=2[C:21]#[N:22])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

3

Reactant 2

HCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 185489534-(3-Chloro-4-fluorophenylamino)-6-fluoro-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 44405398HCID 44405398, compoundYield 71%

Procedure

Following the procedure described above in Example 34, 4-(3-Chloro-4-fluoro-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile was reacted with 3-(4-methylpiperazin-1-yl)propan-1-amine. The crude product was purified by flash column chromatography (10% methanol in methylene chloride) to give a yellow solid (0.102 g, 71%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.8 (m, 2 H) 2.2 (s, 3 H) 2.4 (m, 8 H) 3.3 (m, 4 H) 6.9 (m, 2 H) 7.4 (s, 1 H) 7.5 (t, J=9.0 Hz, 1 H) 7.6 (d, J=7.1 Hz, 1 H) 8.3 (s, 1 H) 8.8 (s, 1 H) 9.7 (s, 1 H).

Workup

  1. customThe crude product was purified by flash column chromatography (10% methanol in methylene chloride)

Sources & evidence

ORD record
ord-aec551ca2a094d0db0e4402498f901cb
Source dataset
uspto-grants-2008_10
Patent number
US07432279B2

Reaction notes

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