3-(Methanesulfonylmethyl)aniline → N5-[2-(3-Methanesulfonylmethyl-phenylamino)-pyrimidin-4-yl]-1,N2,N5-trimethyl-1H-benzoimidazole-2,5-diamine
Reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:21])[C:9]2[CH:20]=[CH:19][C:12]3[N:13]([CH3:18])[C:14]([NH:16][CH3:17])=[N:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:22][S:23]([CH2:26][C:27]1[CH:28]=[C:29]([NH2:33])[CH:30]=[CH:31][CH:32]=1)(=[O:25])=[O:24]>>[CH3:22][S:23]([CH2:26][C:27]1[CH:28]=[C:29]([NH:33][C:2]2[N:7]=[C:6]([N:8]([CH3:21])[C:9]3[CH:20]=[CH:19][C:12]4[N:13]([CH3:18])[C:14]([NH:16][CH3:17])=[N:15][C:11]=4[CH:10]=3)[CH:5]=[CH:4][N:3]=2)[CH:30]=[CH:31][CH:32]=1)(=[O:24])=[O:25]Participants
3
Procedure
The title compound was prepared following the procedure of Example 1 with N5-(2-chloropyrimidin-4-yl)-N2,N5,1-trimethyl-1H-benzimidazole-2,5-diamine (48 mg, 0.16 mmol) and 3-methanesulfonylmethyl-phenylamine (30 mg, 0.16 mmol) as a white solid (75 mg, 83%). 1H NMR (300 MHz, d6-DMSO) δ 9.23 (s, 1H), 7.89 (s, 1H), 7.79 (d, J=6.0 Hz, 1H), 7.68 (d, J=8.1 Hz, 1H), 7.19-7.27 (m, 3H), 7.13 (s, 1H), 6.87-6.93 (m, 2H), 5.66 (d, J=6.0 Hz, 1H), 4.33 (s, 2H), 3.54 (s, 3H), 3.43 (s, 3H), 2.93 (d, J=4.5 Hz, 3H), 2.89 (s, 3H). MS (ESI) m/z=452 [M+H]+.
Sources & evidence
- ORD record
- ord-71d20d9d096a48e5b8b245a92abfb857
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07338959B2
Reaction notes
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