5-Methyl-2-phenylsulfanyl-phenylamine → HCID 24897974, compound

HRID 2197716Notes

Reaction equation

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

Participants

Reactant 2

HCID 433496035-Methyl-2-phenylsulfanyl-phenylamine

HCID 68459349HCID 68459349, compound

Product 1

HCID 24897974HCID 24897974, compound

Procedure

The product from Example 8b (0.098 g, 0.475 mmol) was reacted with the product from Example 1f (0.102 g, 0.475 mmol) for 18 h following the procedure from Example 1g to give the title compound, which was purified by HPLC with TFA. Converted to the hydrochloride salt by treatment with 4N HCl in dioxane at room temperature gave the hydrochloride salt (0.076 g, 38%). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.37 (d, J=6.99 Hz, 6H) 2.38 (s, 3H) 3.30 (m, 1H) 6.32 (d, J=6.99 Hz, 1H) 7.24 (s, 5H) 7.34 (m, 3H) 7.86 (d, J=8.82 Hz, 1H) 8.39 (d, J=7.35 Hz, 1H) 9.08 (d, J=8.46 Hz, 1H) 11.16 (s, 1H) 14.36 (m, 1H); MS (ESI+) m/z 386.0 (M+H)+.

Sources & evidence

ORD record: ord-31f4300eae264b5e93d978fb930de68d
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08338605B2

Reaction notes

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