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

HRID 1391622Notes

Reaction equation

HRID 1391622 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]([CH3:26])[C:9]2[CH:25]=[CH:24][C:12]3[N:13]([CH3:23])[C:14]([NH:16][CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)=[N:15][C:11]=3[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:27][S:28]([CH2:31][C:32]1[CH:38]=[CH:37][C:35]([NH2:36])=[CH:34][CH:33]=1)(=[O:30])=[O:29]>>[CH:17]1([NH:16][C:14]2[N:13]([CH3:23])[C:12]3[CH:24]=[CH:25][C:9]([N:8]([C:6]4[CH:5]=[CH:4][N:3]=[C:2]([NH:36][C:35]5[CH:37]=[CH:38][C:32]([CH2:31][S:28]([CH3:27])(=[O:30])=[O:29])=[CH:33][CH:34]=5)[N:7]=4)[CH3:26])=[CH:10][C:11]=3[N:15]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

3

Reactant 2

HCID 128439644-[(methylsulfonyl)methyl]aniline(SALTDATA: FREE)HCID 59674146HCID 59674146, compound

Product 1

HCID 10311561n2-Cyclohexyl-n5-[2-(4-methanesulfonylmethyl-phenylamino)-pyrimidin-4-yl]-1,n5-dimethyl-1h-benzoimidazole-2,5-diamine

Procedure

The title compound was prepared following the procedure of example 1 with N5-(2-Chloro-pyrimidin-4-yl)-N2-cyclohexyl-1,N5-dimethyl-1H-benzoimidazole-2,5-diamine (92 mg, 0.25 mmol) and 4-[(methylsulfonyl)methyl]aniline (46 mg, 0.25 mmol) as a white solid (31 mg, 24%). 1H NMR (300 MHz, D6-DMSO) δ 9.20 (s, 1H), 7.77-7.80 (M, 3H), 7.10 (s, 1H), 6.82 (d, J=7.8 Hz, 1H), 6.50 (d, J=7.5 Hz, 1H), 5.64 (d, J=6.0 Hz, 1H), 4.34 (s, 2H), 3.70 (br s, 1H), 3.51 (s, 3H), 3.44 (s, 3H), 2.85 (s, 3H), 2.01 (br s, 2H), 1.74 (br s, 2H), 1.62 (d, J=11.1 Hz, 1H), 1.16-1.32 (m, 5H) ppm. MS (ESI) m/z=520 [M+H]+.

Sources & evidence

ORD record
ord-74c506a4d3ac4c55b661411ce65e9d91
Source dataset
uspto-grants-2008_03
Patent number
US07338959B2

Reaction notes

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