N-(3-Aminopropyl)morpholine → HCID 44405456, compound

HRID 2113586Notes

Reaction equation

HRID 2113586 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].[O:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][CH2:31][NH2:32])[CH2:25][CH2:24]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:32][CH2:31][CH2:30][CH2:29][N:26]4[CH2:27][CH2:28][O:23][CH2:24][CH2:25]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 61055N-(3-Aminopropyl)morpholineHCID 185489534-(3-Chloro-4-fluorophenylamino)-6-fluoro-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 44405456HCID 44405456, compoundYield 65%

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-morpholinopropan-1-amine. The crude product was purified by flash column chromatography (5% methanol in methylene chloride) to give a yellow solid (0.065 g, 65%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.8 (m, 2 H) 2.4 (d, J=13.1 Hz, 6 H) 3.3 (dd, J=12.9, 6.8 Hz, 2 H) 3.6 (m, 4 H) 6.9 (m, 2 H) 7.3 (m, 1 H) 7.5 (t, J=9.0 Hz, 1 H) 7.6 (dd, J=6.8, 2.5 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 (5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-785792288f0e451b910ac6fd6587bd42
Source dataset
uspto-grants-2008_10
Patent number
US07432279B2

Reaction notes

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