Triethylamine → HCID 86611448, compound

HRID 1865132Notes

Reaction equation

C(N(CC)CC)C.[CH2:8]([O:10][C:11]([C:13]1[N:14]([CH3:30])[C:15]([CH2:28][CH3:29])=[C:16]([C:26]#[N:27])[C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][OH:25])=[CH:20][CH:19]=1)=[O:12])[CH3:9].[CH3:31][S:32](Cl)(=[O:34])=[O:33]>ClCCl>[CH2:8]([O:10][C:11]([C:13]1[N:14]([CH3:30])[C:15]([CH2:28][CH3:29])=[C:16]([C:26]#[N:27])[C:17]=1[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][O:25][S:32]([CH3:31])(=[O:34])=[O:33])=[CH:20][CH:19]=1)=[O:12])[CH3:9]

Participants

Conditions

Temperature: 0 °C

Procedure

Add triethyl amine (0.053 g, 0.53 mmol) to a solution of 4-cyano-5-ethyl-3(4-hydroxymethyl-phenyl)-1-methyl-1H-pyrrole-2-carboxylic acid ethyl ester (0.15 g, 0.48 mmol, prepared directly above) in dichloromethane (5 mL) at 0° C. under nitrogen, followed by drop-wise addition of methanesulfonyl chloride (0.06 g, 0.53 mmol). Stir at 0° C. for 1.5 h. Add ice-water and dichloromethane. Separate phases and wash organics with water. Combine aqueous layers and back-extract aqueous phase with more dichloromethane. Combine organic phases, wash with brine, dry (sodium sulfate), filter and concentrate in vacuo, to give 0.181 g of title compound for use without further purification. 1H NMR (CDCl3, δ (ppm)): 7.46-7.38 (m, 4H); 5.28 (s, 2H), 4.09 (q, J=7.1 Hz, 2H); 3.89 (s, 3H); 2.93 (s, 3H); 2.85 (q, J=7.5 Hz, 2H); 1.30 (t, J=7.7 Hz, 3H); 1.00 (t, J=7.1 Hz, 3H).

Workup

washSeparate phases and wash organics with water
extractionCombine aqueous layers and back-extract aqueous phase with more dichloromethane
washCombine organic phases, wash with brine
dry with materialdry (sodium sulfate)
filtrationfilter
concentrationconcentrate in vacuo

Sources & evidence

ORD record: ord-fb457db404ba480dba3fc713816ff3c0
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625932B2

Reaction notes

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