4-[(methylsulfonyl)methyl]aniline(SALTDATA: FREE) → n5-[2-(4-Methanesulfonylmethyl-phenylamino)-pyrimidin-4-yl]-1,n5-dimethyl-n2-(4-methyl-benzyl)-1h-benzoimidazole-2,5-diamine hydrochloride
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:28])[C:9]2[CH:27]=[CH:26][C:12]3[N:13]([CH3:25])[C:14]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=4)=[N:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:29][S:30]([CH2:33][C:34]1[CH:40]=[CH:39][C:37]([NH2:38])=[CH:36][CH:35]=1)(=[O:32])=[O:31]>>[ClH:1].[CH3:29][S:30]([CH2:33][C:34]1[CH:40]=[CH:39][C:37]([NH:38][C:2]2[N:7]=[C:6]([N:8]([CH3:28])[C:9]3[CH:27]=[CH:26][C:12]4[N:13]([CH3:25])[C:14]([NH:16][CH2:17][C:18]5[CH:19]=[CH:20][C:21]([CH3:24])=[CH:22][CH:23]=5)=[N:15][C:11]=4[CH:10]=3)[CH:5]=[CH:4][N:3]=2)=[CH:36][CH:35]=1)(=[O:31])=[O:32]Participants
3
Procedure
The title compound was prepared following the procedure of example one with N5-(2-Chloro-pyrimidin-4-yl)-1,N5-dimethyl-N2-(4-methyl-benzyl)-1H-benzoimidazole-2,5-diamine (98 mg, 0.25 mmol) and 4-[(methylsulfonyl)methyl]aniline (46 mg, 0.25 mmol) as a white solid (141 mg, 97%). 1H NMR (300 MHz, d6-DMSO+NaHCO3) δ 9.21 (s, 1H), 7.76-7.79 (M, 3H), 7.50 (br s, 1H), 7.22-7.30 (m, 5H), 7.09-7.14 (M, 3H), 6.86 (d, J=8.4 Hz, 1H), 5.64 (d, J=6.0 Hz, 1H), 4.55 (d, J=5.4 Hz, 2H), 4.34 (s, 2H), 3.58 (s, 3H), 3.43 (s, 3H), 2.85 (s, 3H), 2.26 (s, 3H). MS (ESI) m/z=542 [M+H].
Sources & evidence
- ORD record
- ord-2475a70ff78c4e638f924400f1c8d2d1
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07338959B2
Reaction notes
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