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

HRID 2358604Notes

Reaction equation

HRID 2358604 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.[F:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=2[NH2:28])=[CH:16][CH:15]=1>>[F:13][C:14]1[CH:19]=[CH:18][C:17]([S:20][C:21]2[CH:26]=[CH:25][C:24]([CH3:27])=[CH:23][C:22]=2[NH:28][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:16][CH:15]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 431689322-(4-Fluoro-phenylsulfanyl)-5-methyl-phenylamine

Product 1

HCID 68460843[2-(4-Fluoro-phenylsulfanyl)-5-methyl-phenyl]-(7-methyl-[1,8]naphthyridin-4-yl)-amine

Procedure

The product from Example 1d (167 mg, 0.94 mmol) was reacted with the product from Example 49b (218 mg, 0.94 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 (224 mg, 49%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.37 (m, 3H) 2.77 (m, 3H) 6.29 (d, J=6.99 Hz, 1H) 7.10 (m, 2H) 7.32 (m, 5H) 7.80 (d, J=8.46 Hz, 1H) 8.41 (d, J=6.99 Hz, 1H) 8.95 (d, J=8.46 Hz, 1H) 11.04 (br. s., 1H) 14.43 (br. s., 1H); MS (ESI+) m/z 376 (M+H)+.

Sources & evidence

ORD record
ord-c2ee995d11534cdf9a9f267d73d1d64d
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

Loading…