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

HRID 2358672Notes

Reaction equation

HRID 2358672 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.[Br:13][C:14]1[CH:15]=[CH:16][C:17]([S:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([NH2:20])[CH:19]=1>>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([S:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([NH:20][C:2]2[C:3]3[C:8](=[N:7][C:6]([CH3:12])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)[CH:19]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 284015215-Bromo-2-(phenylthio)benzenamine

Product 1

HCID 68461939(5-Bromo-2-phenylsulfanyl-phenyl)-(7-methyl-[1,8]naphthyridin-4-yl)-amine

Procedure

The product from Example 1d (278 mg, 1.56 mmol) was reacted with the product from Example 121c (437 mg, 1.56 mmol) for 18 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the product as a trifluoroacetic acid (129 mg, 15%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.77 (s, 3H) 6.43 (d, J=6.99 Hz, 1 H) 7.20 (d, J=8.46 Hz, 1 H) 7.34 (s, 5 H) 7.69 (dd, J=8.82, 2.21 Hz, 1 H) 7.81 (m, 2 H) 8.47 (d, J=6.99 Hz, 1 H) 8.95 (d, J=8.46 Hz, 1 H); MS (ESI+) m/z 422 (M+H−TFA)+.

Sources & evidence

ORD record
ord-00a284df157f45ec831b46aa0683c32f
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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