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

HRID 2358554Notes

Reaction equation

HRID 2358554 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-cd6aa2bd6c8e4a07b33506ed381da4ea
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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