4-[(methylsulfonyl)methyl]aniline(SALTDATA: FREE) → n5-[2-(4-Methanesulfonylmethyl-phenylamino)-pyrimidin-4-yl]-n2-(4-methoxy-benzyl)-1,n5-dimethyl-1h-benzoimidazole-2,5-diamine hydrochloride
Reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]([CH3:29])[C:9]2[CH:28]=[CH:27][C:12]3[N:13]([CH3:26])[C:14]([NH:16][CH2:17][C:18]4[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=4)=[N:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:30][S:31]([CH2:34][C:35]1[CH:41]=[CH:40][C:38]([NH2:39])=[CH:37][CH:36]=1)(=[O:33])=[O:32]>>[ClH:1].[CH3:30][S:31]([CH2:34][C:35]1[CH:41]=[CH:40][C:38]([NH:39][C:2]2[N:7]=[C:6]([N:8]([CH3:29])[C:9]3[CH:28]=[CH:27][C:12]4[N:13]([CH3:26])[C:14]([NH:16][CH2:17][C:18]5[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=5)=[N:15][C:11]=4[CH:10]=3)[CH:5]=[CH:4][N:3]=2)=[CH:37][CH:36]=1)(=[O:32])=[O:33]Participants
3
Procedure
The title compound was prepared following the procedure of example two with N5-(2-chloro-pyrimidin-4-yl)-N2-(4-methoxy-benzyl)-1,N5-dimethyl-1H-benzoimidazole-2,5-diamine (82 mg, 0.20 mmol) and 4-[(methylsulfonyl)methyl]aniline (37 mg, 0.20 mmol) as a white solid (86 mg, 72%). 1H NMR (300 MHz, d6-DMSO) δ 9.21 (s, 1H), 7.76-7.81 (m, 3H), 7.29-7.34 (m, 3H), 7.21-7.25 (m, 3H), 7.09 (d, J=1.8 Hz, 1H), 6.82-6.90 (M, 3H), 5.64 (d, J=6.0 Hz, 1H), 4.52 (d, J=5.7 Hz, 2H), 4.35 (s, 2H), 3.72 (s, 3H), 3.56 (s, 3H), 3.43 (s, 3H), 2.85 (s, 3H). MS (ESI) m/z=558 [M+H]+.
Sources & evidence
- ORD record
- ord-f68a2ce7e6e642429560b4e74c343e02
- Source dataset
- uspto-grants-2008_03
- Patent number
- US07338959B2
Reaction notes
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