4-(2-Amino-4-methyl-phenylsulfanyl)-phenol → HCID 68456718, compound

HRID 2358565Notes

Reaction equation

HRID 2358565 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.[NH2:15][C:16]1[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=1[S:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=1>>[CH:12]([C:6]1[N:7]=[C:8]2[C:3]([C:2]([NH:15][C:16]3[CH:21]=[C:20]([CH3:22])[CH:19]=[CH:18][C:17]=3[S:23][C:24]3[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][CH:25]=3)=[CH:11][CH:10]=[N:9]2)=[CH:4][CH:5]=1)([CH3:14])[CH3:13]

Participants

3

Reactant 2

HCID 668081234-(2-Amino-4-methyl-phenylsulfanyl)-phenolHCID 68459349HCID 68459349, compound

Product 1

HCID 68456718HCID 68456718, compound

Procedure

The product from Example 8b (100 mg, 0.435 mmol) was reacted with the product from Example 4c (105 mg, 0.435 mmol) for 18 h following the procedure from Example 1g producing the crude title compound that was purified by HPLC with TFA giving the trifluoroacetic acid salt (90 mg, 47%). 1H NMR (300 MHz, DMSO-d6) δ ppm: 0.97 (d, J=6.62 Hz, 6H), 2.13-2.30 (m, 1H), 2.33 (s, 3H), 2.89 (d, J=6.99 Hz, 2H), 6.29 (d, J=6.99 Hz, 1H), 6.73 (d, J=8.46 Hz, 2H), 7.00 (d, J=8.09 Hz, 1H), 7.13-7.34 (m, 4H), 7.81 (d, J=8.46 Hz, 1H), 8.43 (d, J=6.99 Hz, 1H), 9.03 (d, J=8.46 Hz, 1H), 10.99 (br. s., 1H), 14.36 (br. s., 1H); MS ESI+ m/z 416 (M+H)+; ESI− m/z 414 (M−H)−.

Sources & evidence

ORD record
ord-f1ada9be4fe046039ae3021752a657a7
Source dataset
uspto-grants-2010_07
Patent number
US07763731B2

Reaction notes

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