4-[(methylsulfonyl)methyl]aniline(SALTDATA: FREE) → n2-(4-Fluoro-benzyl)-n5-[2-(4-methanesulfonylmethyl-phenylamino)-pyrimidin-4-yl]-1,n5-dimethyl-1h-benzoimidazole-2,5-diamine hydrochloride

HRID 1391563Notes

Reaction equation

HRID 1391563 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]([F: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].[F:24][C:21]1[CH:22]=[CH:23][C:18]([CH2:17][NH:16][C:14]2[N:13]([CH3:25])[C:12]3[CH:26]=[CH:27][C:9]([N:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:38][C:37]5[CH:39]=[CH:40][C:34]([CH2:33][S:30]([CH3:29])(=[O:32])=[O:31])=[CH:35][CH:36]=5)[N:7]=4)[CH3:28])=[CH:10][C:11]=3[N:15]=2)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 128439644-[(methylsulfonyl)methyl]aniline(SALTDATA: FREE)HCID 59674181N5-(2-chloro-pyrimidin-4-yl)-N2-(4-fluoro-benzyl)-1,N5-dimethyl-1H-benzoimidazole-2,5-diamine

Product 1

HCID 10289896n2-(4-Fluoro-benzyl)-n5-[2-(4-methanesulfonylmethyl-phenylamino)-pyrimidin-4-yl]-1,n5-dimethyl-1h-benzoimidazole-2,5-diamine hydrochloride

Procedure

The title compound was prepared following the procedure of example two with N5-(2-chloro-pyrimidin-4-yl)-N2-(4-fluoro-benzyl)-1,N5-dimethyl-1H-benzoimidazole-2,5-diamine (99 mg, 0.25 mmol) and 4-[(methylsulfonyl)methyl]aniline (46 mg, 0.25 mmol) as a white solid (69 mg, 48%). 1H NMR (300 MHz, d6-DMSO) δ 9.20 (s, 1H), 7.76-7.80 (m, 3H), 7.41-7.46 (m, 3H), 7.23 (d, J=8.4 Hz, 3H), 7.09-7.17 (m, 3H), 6.84 (dd, J=8.4 and 1.8 Hz, 1H), 5.63 (d, J=6.0 Hz, 1H), 4.57 (d, J=5.7 Hz, 2H), 4.34 (s, 2H), 3.57 (s, 3H), 3.43 (s, 3H), 2.85 (s, 3H). MS (ESI) m/z=546 [M+H]+.

Sources & evidence

ORD record
ord-92dc08b897f646deba16374dbf737e36
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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