5-Chloro-2-methyl-1,8-naphthyridine → (7-Methyl-[1,8]naphthyridin-4-yl)-(5-methyl-2-p-tolylsulfanyl-phenyl)-amine

HRID 2197763Notes

Reaction equation

HRID 2197763 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH3:12])=[N:7]2.[CH3:13][C:14]1[CH:15]=[CH:16][C:17]([S:21][C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)=[C:18]([NH2:20])[CH:19]=1>>[CH3:12][C:6]1[N:7]=[C:8]2[C:3]([C:2]([NH:20][C:18]3[CH:19]=[C:14]([CH3:13])[CH:15]=[CH:16][C:17]=3[S:21][C:22]3[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=3)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:5]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 431689305-Methyl-2-p-tolylsulfanyl-phenylamine

Product 1

HCID 68460860(7-Methyl-[1,8]naphthyridin-4-yl)-(5-methyl-2-p-tolylsulfanyl-phenyl)-amine

Procedure

The product from Example 1d (267 mg, 1.56 mmol) was reacted with the product from Example 47b (358 mg, 1.56 mmol) for 48 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the trifluoroacetic acid salt (347 mg, 46%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.22 (s, 3H) 2.37 (s, 3H) 2.77 (s, 3H) 6.27 (d, J=7.35 Hz, 1H) 7.04 (d, J=7.72 Hz, 2H) 7.14 (m, 2H) 7.29 (m, 3H) 7.79 (d, J=8.82 Hz, 1H) 8.39 (d, J=6.99 Hz, 1H) 8.95 (d, J=8.46 Hz, 1H) 11.25 (br. s., 1H) 14.39 (br. s., 1H); MS (ESI+) m/z 372 (M+H)+.

Sources & evidence

ORD record
ord-e1b51e1139924ae494d7d32bb4411c11
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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