2,4-Dichloro-6-methoxy-3,5-triazine → 3,4-Dichloro-N-[1-(4-chloro-6-methoxy-1,3,5-triazin-2-yl)piperidin-4-yl]-5-methyl-1H-pyrrole-2-carboxamide
Reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH3:10])[N:3]=1.Cl.[Cl:12][C:13]1[C:17]([Cl:18])=[C:16]([CH3:19])[NH:15][C:14]=1[C:20]([NH:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)=[O:21]>CN(C=O)C.O>[Cl:12][C:13]1[C:17]([Cl:18])=[C:16]([CH3:19])[NH:15][C:14]=1[C:20]([NH:22][CH:23]1[CH2:28][CH2:27][N:26]([C:2]2[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([O:9][CH3:10])[N:3]=2)[CH2:25][CH2:24]1)=[O:21]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 2,4-dichloro-6-methoxy-1,3,5-triazine (commercially available) (0.05 g, 0.32 mmol) in DMF (0.5 ml) was added to a solution of 3,4-dichloro-5-methyl-N-piperidin-4-yl-1H-pyrrole-2-carboxamide hydrochloride (Intermediate 1, 0.1 g, 0.32 mmol) and TEA (0.06 g, 0.64 mmol) in DMF (1.5 ml). The resultant mixture was stirred for 1 h at room temperature, then was diluted with water and extracted with EtOAc. During the aqueous workup, some of the product precipitated and was collected by suction filtration. The organic extract was dried over magnesium sulphate, filtered and concentrated to give the desired product with small amount of impurities.
Workup
- extractionextracted with EtOAc
- customDuring the aqueous workup, some of the product precipitated
- filtrationwas collected by suction filtration
- extractionThe organic extract
- dry with materialwas dried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-c990d5f92f9d4f1cb7355c4ad80f37b4
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07709503B2
Reaction notes
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