Triethylamine → 3,4-Dichloro-N-[1-(2-chloropyrimidin-4-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide
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].[Cl:19][C:20]1[N:25]=[C:24](Cl)[CH:23]=[CH:22][N:21]=1.CCN(CC)CC>CN(C=O)C.CCOC(C)=O.O>[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:22]2[CH:23]=[CH:24][N:25]=[C:20]([Cl:19])[N:21]=2)[CH2:15][CH2:14]1)=[O:11]Participants
7
Reactant 3
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 90 °C
Procedure
3,4-Dichloro-5-methyl-N-piperidin-4-yl-1H-pyrrole-2-carboxamide hydrochloride (Intermediate 1, 650 mg, 2.08 mmol), 2,4-dichloropyrimidine (309.7 mg, 2.08 mmol), and Et3N (0.6 ml, 4.16 mmol) were combined in DMF (12 ml) and heated at 90° C. under nitrogen for 1.5 h. Upon cooling to room temperature, the reaction was diluted with EtOAc and water. The phases were separated, and the aqueous portion was extracted twice with EtOAc. The combined organic portions were washed with brine, dried over Na2SO4, filtered, and concentrated under reduced pressure to give a light brown solid. The crude material was triturated with cold MeOH and filtered to give 458 mg (1.18 mmol, 57%) of the title product.
Workup
- temperatureUpon cooling to room temperature
- customThe phases were separated
- extractionthe aqueous portion was extracted twice with EtOAc
- washThe combined organic portions were washed with brine
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customto give a light brown solid
- customThe crude material was triturated with cold MeOH
- filtrationfiltered
Sources & evidence
- ORD record
- ord-4efd95c46d8143f1b7a1a4958292d895
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709503B2
Reaction notes
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