Triethylamine → N-methyl-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]-N'-3-thienylurea

HRID 1851591Notes

Reaction equation

Cl.[CH3:2][NH:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)=[CH:9]2.C(N(CC)CC)C.[N:25]([C:28]1[CH:32]=[CH:31][S:30][CH:29]=1)=[C:26]=[O:27]>O1CCCC1>[CH3:2][N:3]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][C:10]([C:13]1[S:14][CH:15]=[CH:16][N:17]=1)=[CH:9]2)[C:26]([NH:25][C:28]1[CH:32]=[CH:31][S:30][CH:29]=1)=[O:27]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of N-methyl-2-(1,3-thiazol-2-yl)-1H-indole-7-amine hydrochloride (50 mg) and triethylamine (35 mL) in tetrahydrofuran (3 mL) was added 3-isocyanatothiophene (26 mg). The reaction mixture was stirred at 50° C. for 1 hr. The reaction mixture was concentrated, and the obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:1) to give the title compound (74 mg, yield 99%) as yellow crystals. melting point 266° C.

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-e7a9e2e855104fb6945a174f7aef7d81
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957070B2

Reaction notes

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