Toluene → HCID 178494102, compound

HRID 470351Notes

Reaction equation

[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[CH:12][C:11]([NH2:14])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.C[Al](C)C.C1(C)C=CC=CC=1.C[O:27][C:28]([C:30]1[CH:53]=[CH:52][C:33]2[N:34]=[C:35]([C:37]3[CH:42]=[C:41]([C:43]4[C:44]([O:49][CH3:50])=[N:45][CH:46]=[CH:47][CH:48]=4)[CH:40]=[CH:39][C:38]=3[OH:51])[NH:36][C:32]=2[CH:31]=1)=O>ClCCCl.C(Cl)Cl.CO>[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[CH:12][C:11]([NH:14][C:28]([C:30]3[CH:53]=[CH:52][C:33]4[NH:34][C:35]([C:37]5[CH:42]=[C:41]([C:43]6[C:44]([O:49][CH3:50])=[N:45][CH:46]=[CH:47][CH:48]=6)[CH:40]=[CH:39][C:38]=5[OH:51])=[N:36][C:32]=4[CH:31]=3)=[O:27])=[CH:10][CH:9]=2)[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 6-(4-methyl-piperazin-1-yl)-pyridin-3-ylamine (38.4 mg, 0.2 mmol) in dry DCE (1 mL) were added AlMe3 in toluene solution (2.0 M, 160 μL, 0.32 mmol), and then 2-[2-hydroxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-3H-benzoimidazole-5-carboxylic acid methyl ester (37.5 mg, 0.1 mmol). The reaction mixture was heated at 80° C. for 16.5 h, cooled to the room, loaded on silica gel, and chromatographyed (250:10:1 CH2Cl2/MeOH/28% aqueous NH4OH) to afford the title compound (10.7 mg, 20%). 1H NMR (MeOH-d4) δ 2.35 (s, 3H), 2.57 (m, 4H), 3.54 (m, 4H), 3.97 (s, 3H), 6.84 (d, J=9 Hz, 1H), 7.03-7.10 (2H), 7.58 (d, J=9 Hz, 1H), 7.68 (d, J=9 Hz, 1H), 7.78 (d, J=9 Hz, 1H), 7.86-7.93 (2H), 8.13 (m, 1H), 8.17 (s, 1H), 8.22 (s, 1H), 8.41 (s, 1H). ESI-MS m/z 536.3 (MH+).

Workup

temperaturecooled to the room

Sources & evidence

ORD record: ord-24c1181856554766b44431681a0566d1
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629147B2

Reaction notes

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