Water → N-{2-[2-(diethylamino)ethylamino]-2-oxoethyl}-5-formyl-2,4-dimethyl-1H-pyrrole-3-formamide

HRID 73254Notes

Reaction equation

Cl.C(N=C=NCCCN(C)C)C.[CH2:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH3:14].[CH:20]([C:22]1[NH:26][C:25]([CH3:27])=[C:24]([C:28]([OH:30])=O)[C:23]=1[CH3:31])=[O:21].O[N:33]1[C:37]2C=CC=C[C:36]=2[N:35]=N1.[OH2:42]>CN(C=O)C>[CH2:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH2:17][NH:35][C:36](=[O:42])[CH2:37][NH:33][C:28]([C:24]1[C:23]([CH3:31])=[C:22]([CH:20]=[O:21])[NH:26][C:25]=1[CH3:27])=[O:30])[CH3:14]

Participants

Conditions

Temperature: 0 °C

Procedure

1-Ethyl-(3-dimethylaminopropyl) carbodiimide hydrochloride (1.074 g, 5.6 mmol), triethylamine (1.12 mL, 8 mmol), 5-formyl-2,4-dimethyl-1H-pyrrole-3-formic acid (0.668 g, 4 mmol) and 1-hydroxybenzotriazole (0.756 g, 5.6 mmol) were added to DMF (10 mL) with stirring at about 0° C. and stirred for 1.5 hrs, and the oily residue obtained in the above step (1.38 g, 8 mmol) was added. The reaction was stirred at room temperature until completion was indicated by thin layer chromatography (TLC). 1.2 mL of water and 1 mL of saturated salt water were added, and the mixture was extracted with organic solvents (10% methanol/dichloromethane) (25 mL×3), the combined organic phase was washed with saturated salt water (25 mL×3), dried over anhydrous Na2SO4, and the solvent was distilled off under reduced pressure. The residue was then chromatographed (silica gel column chromatography, eluent: methanol:ethyl acetate=1:2) to give 0.625 g (1.94 mmol) of N-{2-[2-(diethylamino)ethylamino]-2-oxoethyl}-5-formyl-2,4-dimethyl-1H-pyrrole-3-formamide. Yield 48.5%. 1HNMR (DMSO-d6) δ 10.83 (s, br, 1H, NH), 9.75 (s, 1H), 7.65 (m, br, 1H, CONHCH2), 7.64 (m, br, 1H, CONHCH2), 3.81-3.73 (d, 2H), 3.14-3.10 (m, 2H), 2.57-2.55 (m, 2H), 2.46-2.40 (m, 4H), 2.26-2.20 (s, 3H), 2.12-2.08 (m, 3H), 1.06-1.01 (m, 6H).

Workup

stirringstirred for 1.5 hrs
customthe oily residue obtained in the above step (1.38 g, 8 mmol)
additionwas added
stirringThe reaction was stirred at room temperature until completion
extractionthe mixture was extracted with organic solvents (10% methanol/dichloromethane) (25 mL×3)
washthe combined organic phase was washed with saturated salt water (25 mL×3)
dry with materialdried over anhydrous Na2SO4
distillationthe solvent was distilled off under reduced pressure
customThe residue was then chromatographed (silica gel column chromatography, eluent: methanol:ethyl acetate=1:2)

Sources & evidence

ORD record: ord-8b5a11a0ed18427cb0ae1bae620d9b7a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08829039B2

Reaction notes

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