N,N-Dimethylethylenediamine → Ethyl 5-[[[2-(dimethylamino)ethyl]amino]carbonyl]thiophen-2-carboxylate

HRID 131279Notes

Reaction equation

HRID 131279 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]([OH:13])=O)=[CH:8][CH:7]=1)=[O:5])[CH3:2].[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][NH2:18].ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(N(CC)CC)C.C(Cl)Cl>[CH3:14][N:15]([CH3:19])[CH2:16][CH2:17][NH:18][C:11]([C:9]1[S:10][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][CH:8]=1)=[O:13]

Participants

9

Reactant 5

HCID 66053N,N-DimethylethylenediamineHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 152321235-(Ethoxycarbonyl)thiophene-2-carboxylic acid

Product 1

HCID 69300800Ethyl 5-[[[2-(dimethylamino)ethyl]amino]carbonyl]thiophen-2-carboxylateYield 53%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To 5-(ethoxycarbonyl)thiophen-2-carboxylic acid (250 mg) is added successively methylene chloride (3.0 mL), N,N-dimethylethylenediamine (100 mg), 1-hydroxybenzotriazole (205 mg), triethylamine (610 mg), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (290 mg). The mixture is stirred at room temperature overnight. The reaction mixture is diluted with chloroform and thereto is added a saturated sodium hydrogencarbonate solution. After stirring, the organic layer is separated and concentrated in vacuo. The residue is purified by flash column chromatography on NH-silica gel (Solvent; ethyl acetate) to give ethyl 5-[[[2-(dimethylamino)ethyl]amino]carbonyl]thiophen-2-carboxylate (160 mg, yield; 53%) as brown crystals. MS (APCI) m/z: 271 [M+H]+

Workup

  1. stirringAfter stirring
  2. customthe organic layer is separated
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by flash column chromatography on NH-silica gel (Solvent; ethyl acetate)

Sources & evidence

ORD record
ord-e0567fc9cbdb47f7b986b9d287522a30
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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