4-Methoxybenzylamine → 4-[(3-Isopropylphenyl)amino]-6-[(4-methoxybenzyl)amino]-1,7-naphthyridine-3-carbonitrile

HRID 2113576Notes

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.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][NH2:33])=[CH:28][CH:27]=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:33][CH2:32][C:29]4[CH:30]=[CH:31][C:26]([O:25][CH3:24])=[CH:27][CH:28]=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

Reactant 2

HCID 754524-Methoxybenzylamine

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

Product 1

HCID 693180674-[(3-Isopropylphenyl)amino]-6-[(4-methoxybenzyl)amino]-1,7-naphthyridine-3-carbonitrileYield 25%

Procedure

Following the procedure described above in Example 34, 6-fluoro-4-[(3-isopropylphenyl)amino]-1,7-naphthyridine-3-carbonitrile was reacted with (4-methoxyphenyl)methanamine. The crude product was purified by flash column chromatography (1% methanol in methylene chloride) to give a yellow solid (0.209 g, 25%). 1H NMR (400 MHz, DMSO-D6) δ ppm 1.2 (d, J=6.8 Hz, 6 H) 2.8 (none, 1 H) 2.9 (dq, J=6.9 Hz, 1 H) 3.7 (s, 3 H) 4.4 (d, J=6.3 Hz, 2 H) 6.9 (m, 2 H) 7.1 (m, 2 H) 7.1 (dd, J=4.3, 2.5 Hz, 2 H) 7.3 (m, 4 H) 8.2 (s, 1 H) 8.8 (s, 1 H) 9.6 (s, 1 H)

Workup

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

Sources & evidence

ORD record: ord-b96fac4d617544b387396f0c0b56862c
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432279B2

Reaction notes

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