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

HRID 2197828Notes

Reaction equation

HRID 2197828 reaction equation
Cl[C:2]1[CH:11]=[CH:10][N:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][C:6]([CH2:12][CH:13]([CH3:15])[CH3:14])=[N:7]2.[CH3:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24][C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][C:26]=2[NH2:32])=[CH:20][CH:19]=1>>[CH2:12]([C:6]1[N:7]=[C:8]2[C:3]([C:2]([NH:32][C:26]3[CH:27]=[C:28]([CH3:31])[CH:29]=[CH:30][C:25]=3[S:24][C:21]3[CH:22]=[CH:23][C:18]([O:17][CH3:16])=[CH:19][CH:20]=3)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:5]=1)[CH:13]([CH3:15])[CH3:14]

Participants

3

Reactant 2

HCID 433496162-(4-Methoxy-phenylsulfanyl)-5-methyl-phenylamineHCID 684607201,8-Naphthyridine, 5-chloro-2-(2-methylpropyl)-

Product 1

HCID 68457663(7-Isobutyl-[1,8]naphthyridin-4-yl)-[2-(4-methoxy-phenylsulfanyl)-5-methyl-phenyl]-amine

Procedure

The product from Example 12d (60 mg, 0.271 mmol) was reacted with the product from Example 50b (66 mg, 0.271 mmol) for 25 h giving following the procedure from Example 1g the crude title compound that was triturated with 3:1 ether/THF providing the title compound as a hydrochloride salt (121 mg, 96%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.97 (d, J=6.62 Hz, 6H) 2.24 (m, J=6.62 Hz, 1H) 2.34 (s, 3H) 2.89 (d, J=7.35 Hz, 2H) 3.72 (s, 3H) 6.27 (d, J=6.99 Hz, 1H) 6.84 (d, J=8.46 Hz, 2H) 7.10 (d, J=8.09 Hz, 1H) 7.23-7.32 (m, 4H) 7.81 (d, J=8.46 Hz, 1H) 8.41 (d, J=6.99 Hz, 1H) 9.07 (d, J=8.46 Hz, 1H) 11.09 (br s, 1H) 14.40 (br s, 1H); MS (ESI+) m/z 430 (M−Cl)+; (ESI−) m/z 428 (M−HCl)−.

Workup

  1. customgiving

Sources & evidence

ORD record
ord-e6ce6ccc38864d878a18d8af975f616e
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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