Benzylamine → 4-[(3-Chloro-4-fluorophenyl)amino]-6-[(phenylmethyl)amino]-1,7-naphthyridine-3-carbonitrile

HRID 2113584Notes

Reaction equation

HRID 2113584 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].[CH2:23]([NH2:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH2:23]([NH:30][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][N:16]=1)[N:13]=[CH:12][C:11]([C:21]#[N:22])=[C:10]2[NH:9][C:4]1[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 7504BenzylamineHCID 185489534-(3-Chloro-4-fluorophenylamino)-6-fluoro-1,7-naphthyridine-3-carbonitrile

Product 1

HCID 444054914-[(3-Chloro-4-fluorophenyl)amino]-6-[(phenylmethyl)amino]-1,7-naphthyridine-3-carbonitrileYield 54%

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 benzylamine. The crude product was purified by flash column chromatography (1% methanol in methylene chloride) to give a yellow solid (0.051 g, 54%). 1H NMR (400 MHz, DMSO-D6) δ ppm 4.5 (d, J=6.3 Hz, 2 H) 7.0 (s, 1 H) 7.2 (t, J=7.2 Hz, 1 H) 7.3 (m, 5 H) 7.5 (m, 2 H) 7.6 (dd, J=6.6, 2.5 Hz, 1 H) 8.3 (s, 1 H) 8.9 (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-1b9423c6f577477bb140bb65e73a5821
Source dataset
uspto-grants-2008_10
Patent number
US07432279B2

Reaction notes

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