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

HRID 2197819Notes

Reaction equation

HRID 2197819 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][CH2:13][CH3:14])=[N:7]2.[CH3:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([S:23][C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=2[NH2:31])=[CH:19][CH:18]=1>>[CH3:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([S:23][C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][C:25]=2[NH:31][C:2]2[C:3]3[C:8](=[N:7][C:6]([CH2:12][CH2:13][CH3:14])=[CH:5][CH:4]=3)[N:9]=[CH:10][CH:11]=2)=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 433496162-(4-Methoxy-phenylsulfanyl)-5-methyl-phenylamineHCID 441401765-Chloro-2-propyl-[1,8]naphthyridine

Product 1

HCID 68460687[2-(4-Methoxy-phenylsulfanyl)-5-methyl-phenyl]-(7-propyl-[1,8]naphthyridin-4-yl)-amine

Procedure

The product from Example 2g (275 mg, 1.33 mmol) was reacted with the product from Example 50b (326 mg, 1.33 mmol) for 18 h following the procedure from Example 1g giving the crude title compound which was purified by HPLC with TFA providing the product as a trifluoroacetic acid (392 mg, 56%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.98 (t, J=7.35 Hz, 3H) 1.85 (m, 2H) 2.34 (s, 3H) 3.00 (t, J=7.54 Hz, 2H) 3.72 (s, 3H) 6.27 (d, J=6.99 Hz, 1H) 6.84 (d, J=8.82 Hz, 2H) 7.11 (d, J=7.72 Hz, 1H) 7.27 (m, 4H) 7.83 (d, J=8.82 Hz, 1H) 8.41 (d, J=6.99 Hz, 1H) 9.02 (d, J=8.46 Hz, 1H) 11.06 (br. s., 1H) 14.37 (br. s., 1H); MS (ESI+) m/z 416 (M+H)+.

Sources & evidence

ORD record
ord-b5dcaa9502f24403a62dd09bcdedd925
Source dataset
uspto-grants-2012_12
Patent number
US08338605B2

Reaction notes

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