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

HRID 1851589Notes

Reaction equation

HRID 1851589 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.[C:25]1([C:30](Cl)=[O:31])[S:29][CH:28]=[CH:27][CH:26]=1>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:30]([C:25]1[S:29][CH:28]=[CH:27][CH:26]=1)=[O:31]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 789282-Thiophenecarbonyl chlorideHCID 67109280N-Methyl-2-(1,3-thiazol-2-yl)-1H-indole-7-amine hydrochloride

Product 1

HCID 57901666N-methyl-N-[2-(1,3-thiazol-2-yl)-1H-indol-7-yl]thiophene-2-carboxamideYield 117.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methyl-2-(1,3-thiazol-2-yl)-1H-indole-7-amine hydrochloride (200 mg) in tetrahydrofuran (3 mL) were added triethylamine (100 μL) and 2-thenoyl chloride (100 mg), and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, and the obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:3) to give the title compound (273 mg, yield 92%) as colorless crystals. melting point 250° C.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-ca427f0e23dc43afa6871cef4a1d2a1f
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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