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

HRID 2197772Notes

Reaction equation

HRID 2197772 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][O:14][C:15]1[CH:20]=[CH:19][C:18]([S:21][C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=2[NH2:29])=[CH:17][CH:16]=1>>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([S:21][C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=2[NH:29][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][CH:20]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 433496162-(4-Methoxy-phenylsulfanyl)-5-methyl-phenylamine

Product 1

HCID 68458466[2-(4-Methoxy-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 50b (245 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 (325 mg, 70%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.35 (s, 3H) 2.77 (s, 3H) 3.73 (s, 3H) 6.26 (d, J=6.99 Hz, 1H) 6.85 (d, J=8.82 Hz, 2H) 7.11 (d, J=7.72 Hz, 1H) 7.26 (d, J=8.82 Hz, 2H) 7.31 (s, 1H) 7.80 (d, J=8.46 Hz, 1H) 8.41 (d, J=6.99 Hz, 1H) 8.99 (d, J=8.82 Hz, 1H) 11.04 (br. s., 1H) 14.32 (br. s., 1H); MS ESI+ m/z 388 (M+H)+.

Sources & evidence

ORD record
ord-441352539ea449ed935677a4244b0c4d
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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