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

HRID 2197719Notes

Reaction equation

HRID 2197719 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:7]([NH2:9])[CH:8]=1.Cl[C:18]1[CH:27]=[CH:26][N:25]=[C:24]2[C:19]=1[CH:20]=[CH:21][C:22]([CH3:28])=[N:23]2>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([S:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[C:7]([NH:9][C:18]2[C:19]3[C:24](=[N:23][C:22]([CH3:28])=[CH:21][CH:20]=3)[N:25]=[CH:26][CH:27]=2)[CH:8]=1

Participants

3

Reactant 2

HCID 122663725-Chloro-2-methyl-1,8-naphthyridineHCID 13500181HCID 13500181, compound

Product 1

HCID 68457898(5-Methoxy-2-phenylsulfanyl-phenyl)-(7-methyl-[1,8]naphthyridin-4-yl)-amine

Procedure

The product from Example 9b (69 mg, 0.30 mmol) was reacted with the product from Example 1d (53 mg, 0.30 mmol) following the procedure from Example 1g giving the title compound as a hydrochloride salt after trituration with solid (119 mg, 96%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 2.75 (s, 3H) 3.83 (s, 3H) 6.34 (d, J=6.99 Hz, 1H) 7.07 (m, 7H) 7.57 (d, J=8.46 Hz, 1H) 7.76 (d, J=8.46 Hz, 1H) 8.85 (d, J=6.99 Hz, 1H) 8.99 (d, J=8.46 Hz, 1H) 11.16 (br s, 1H) 14.43 (brs, 1H); MS (ESI+) m/z 374 (M−Cl)+; (ESI−) m/z 372 (M−HCl)−.

Sources & evidence

ORD record
ord-34688502cfcc46c79a790e5b643e07bb
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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