Potassium Carbonate → 4-Methyl-2-{6-chloro-2-[4-(3-trifluoromethoxyphenyl)-imidazol-1-yl]-pyrimidin-4-ylamino}-pentanoic acid (3-ethoxypropyl)amide

HRID 1822813Notes

Reaction equation

HRID 1822813 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:23])[CH:9]([NH:14][C:15]1[CH:20]=[C:19]([Cl:21])[N:18]=[C:17](Cl)[N:16]=1)[CH2:10][CH:11]([CH3:13])[CH3:12])[CH3:2].[F:24][C:25]([F:39])([F:38])[O:26][C:27]1[CH:28]=[C:29]([C:33]2[N:34]=[CH:35][NH:36][CH:37]=2)[CH:30]=[CH:31][CH:32]=1.C([O-])([O-])=O.[K+].[K+].[F-].[K+]>CS(C)=O.O>[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:23])[CH:9]([NH:14][C:15]1[CH:20]=[C:19]([Cl:21])[N:18]=[C:17]([N:36]2[CH:37]=[C:33]([C:29]3[CH:30]=[CH:31][CH:32]=[C:27]([O:26][C:25]([F:24])([F:38])[F:39])[CH:28]=3)[N:34]=[CH:35]2)[N:16]=1)[CH2:10][CH:11]([CH3:13])[CH3:12])[CH3:2]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 522689Potassium FluorideHCID 235685972-(2,6-Dichloropyrimidin-4-ylamino)-4-methylpentanoic acid (3-ethoxypropyl)amideHCID 178506377HCID 178506377, compound

Product 1

HCID 865921684-Methyl-2-{6-chloro-2-[4-(3-trifluoromethoxyphenyl)-imidazol-1-yl]-pyrimidin-4-ylamino}-pentanoic acid (3-ethoxypropyl)amideYield 122.2%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of 2-(2,6-dichloro-pyrimidin-4-ylamino)-4-methylpentanoic acid (3-ethoxypropyl)amide (1.5 gram), 4-(3-trifluoromethoxyphenyl)-1H-imidazole (0.99 gram), K2CO3 (1.7 gram) and KF (0.24 gram) in dimethylsulfoxide (40 ml) was heated to 100° C. for 17 hours. The solution was cooled to room temperature, taken up in water, and extracted three times with ethyl acetate. The etyl acetate layers were combined, washed with brine, dried over magnesium sulfate, filtered, and the solvents were removed in vacuo. Silica gel chromatography (toluene/acetone 4/1) provided 2.8 g of 4-methyl-2-{6-chloro-2-[4-(3-trifluoromethoxyphenyl)-imidazol-1-yl]-pyrimidin-4-ylamino}-pentanoic acid (3-ethoxypropyl)amide as an orange oil.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvents were removed in vacuo

Sources & evidence

ORD record
ord-70bc9e88f8b74a86908c6db1efc44a3e
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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