Water → HCID 68582033, compound

HRID 2233997Notes

Reaction equation

Cl.[Cl:2][C:3]1[C:7]([Cl:8])=[C:6]([CH3:9])[NH:5][C:4]=1[C:10]([NH:12][CH:13]1[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1)=[O:11].Br[C:20]1[S:21][C:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:23]([CH3:25])[N:24]=1.C(=O)(O)[O-].[Na+].O>CN(C=O)C>[Cl:2][C:3]1[C:7]([Cl:8])=[C:6]([CH3:9])[NH:5][C:4]=1[C:10]([NH:12][CH:13]1[CH2:18][CH2:17][N:16]([C:20]2[S:21][C:22]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:23]([CH3:25])[N:24]=2)[CH2:15][CH2:14]1)=[O:11]

Participants

Conditions

Temperature: 50 °C

Procedure

3,4-Dichloro-5-methyl-N-piperidin-4-yl-1H-pyrrole-2-carboxamide hydrochloride (Intermediate 1; 0.500 g, 2.00 mmol), ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate (0.625 g, 2.00 mmol) and sodium bicarbonate (0.336 g, 2.00 mmol) were stirred in DMF (5 ml). The reaction was heated to 50° C. overnight. The solution was diluted by the addition of water and the resulting layers were separated. The aqueous layer was extracted with EtOAc (3×), and the organic layers were combined, dried over anhydrous magnesium sulfate, filtered and concentrated. Hexanes were added to the crude material, and the precipitate was filtered and rinsed with EtOAc to give the title compound as a beige solid (0.273 g).

Workup

customthe resulting layers were separated
extractionThe aqueous layer was extracted with EtOAc (3×)
dry with materialdried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated
additionHexanes were added to the crude material
filtrationthe precipitate was filtered
washrinsed with EtOAc

Sources & evidence

ORD record: ord-c4f4974fe98e4224aa282594f234ca0b
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709503B2

Reaction notes

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