Water → HCID 178499026, compound

HRID 2233907Notes

Reaction equation

HRID 2233907 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[N:3]=1.Cl.[Cl:14][C:15]1[C:19]([Cl:20])=[C:18]([CH3:21])[NH:17][C:16]=1[C:22]([NH:24][CH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:23].O>CN(C=O)C>[Cl:1][C:2]1[NH:3][C:4]([N:28]2[CH2:27][CH2:26][CH:25]([NH:24][C:22]([C:16]3[NH:17][C:18]([CH3:21])=[C:19]([Cl:20])[C:15]=3[Cl:14])=[O:23])[CH2:30][CH2:29]2)([C:9]([O:11][CH3:12])=[O:10])[CH:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 239689Methyl 2,4-dichloropyrimidine-6-carboxylateHCID 68579996HCID 68579996, compound2×

Product 1

HCID 178499026HCID 178499026, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of methyl 2,4-dichloropyrimidine-6-carboxylate (commercially available) (0.95 g, 4.6 mmol) in DMF (5 ml) was added dropwise to a solution of 3,4-dichloro-5-methyl-N-piperidin-4-yl-1H-pyrrole-2-carboxamide hydrochloride (Intermediate 1, 0.43 g, 4.6 mmol) and TEA (0.92 g, 9.2 mmol) in DMF (10 ml) under nitrogen. The resultant mixture was stirred for 1 h at room temperature. Water (50 ml) was added to the stirred reaction mixture and the material that precipitated was collected and washed with water/acetonitrile (1:1, 15 ml) to give 1.9 g of the title compound. An analytical sample was purified by reversed-phase HPLC (water/acetonitrile gradient, 20-95%).

Workup

  1. customthe material that precipitated
  2. customwas collected
  3. washwashed with water/acetonitrile (1:1, 15 ml)

Sources & evidence

ORD record
ord-f0446d0cc9aa48948a87b55058304e1e
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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