Pyridine → 1-Methyl-1H-imidazole-4-sulfonic acid (4-chloro-benzyl)-(2-ethyl-1-oxo-2,3-dihydro-1H-isoindol-5-yl)-amide

HRID 1947632Notes

Reaction equation

[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][NH:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[N:12]([CH2:18][CH3:19])[CH2:11]3)=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:28][N:29]1[CH:33]=[C:32]([S:34](Cl)(=[O:36])=[O:35])[N:31]=[CH:30]1>C(#N)C>[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[N:12]([CH2:18][CH3:19])[CH2:11]3)[S:34]([C:32]2[N:31]=[CH:30][N:29]([CH3:28])[CH:33]=2)(=[O:36])=[O:35])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a stirred solution of 5-(4-Chloro-benzylamino)-2-ethyl-2,3-dihydro-isoindol-1-one (40 mg, 0.133 mmol) and pyridine (23 μM, 0.29 mmol) in dry acetonitrile (1 ml) was added 1-methyl-1H-imidazole-4-sulfonyl chloride (52 mg, 0.29 mmol) and the reaction heated to 150° C. in a microwave for 0.5 hrs. The reaction was filtered and purified by preparative HPLC (Method B) to afford the title compound as an off white solid (17 mg, 25%). HPLC retention time 4.00 min. Mass spectrum (ES+) m/z 445 (M+H).

Workup

filtrationThe reaction was filtered
custompurified by preparative HPLC (Method B)

Sources & evidence

ORD record: ord-1eabab13172e48e5a490ef452e7c0482
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399481B2

Reaction notes

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