2-Morpholinoethylamine → 4-[(3-Isopropylphenyl)amino]-6-[(2-morpholin-4-ylethyl)amino]-1,7-naphthyridine-3-carbonitrile

HRID 2113575Notes

Reaction equation

HRID 2113575 reaction equation
F[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][N:11]=1)[N:8]=[CH:7][C:6]([C:12]#[N:13])=[C:5]2[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]([CH3:23])[CH3:22])[CH:16]=1.[N:24]1([CH2:30][CH2:31][NH2:32])[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1>N1C=CC=CC=1>[CH:21]([C:17]1[CH:16]=[C:15]([NH:14][C:5]2[C:4]3[C:9](=[CH:10][N:11]=[C:2]([NH:32][CH2:31][CH2:30][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)[CH:3]=3)[N:8]=[CH:7][C:6]=2[C:12]#[N:13])[CH:20]=[CH:19][CH:18]=1)([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 4082852-MorpholinoethylamineHCID 691808106-Fluoro-4-[(3-isopropylphenyl)amino]-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 693183754-[(3-Isopropylphenyl)amino]-6-[(2-morpholin-4-ylethyl)amino]-1,7-naphthyridine-3-carbonitrileYield 54%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Following the procedure described above in Example 34, 6-fluoro-4-[(3-isopropylphenyl)amino]-1,7-naphthyridine-3-carbonitrile was reacted with 2-morpholin-4-yl-ethylamine in pyridine. The crude product was purified by flash column chromatography (1% methanol in methylene chloride) to give a yellow solid (0.15 g, 54%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.2 (d, J=7.1 Hz, 6 H) 2.4 (m, 4 H) 2.6 (m, 2 H) 2.9 (dq, J=6.9 Hz, 1 H) 3.4 (m, 2 H) 3.6 (m, 4 H) 6.6 (t, J=5.4 Hz, 1 H) 7.1 (m, 4 H) 7.3 (t, J=8.0 Hz, 1 H) 8.2 (s, 1 H) 8.8 (s, 1 H) 9.6 (s, 1 H)

Workup

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

Sources & evidence

ORD record
ord-e92871290d3a4b7bbe75ff4d0b9c2fe8
Source dataset
uspto-grants-2008_10
Patent number
US07432279B2

Reaction notes

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