Water → 4-Methyl-2-{6-(4,4,4-trifluorobutoxy)-2-[4-(4-trifluoromethoxyphenyl)-imidazol-1-yl]pyrimidin-4-ylamino}pentanoic acid (3-ethoxypropyl) amide

HRID 1822814Notes

Reaction equation

HRID 1822814 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:38])[CH:9]([NH:14][C:15]1[CH:20]=[C:19](Cl)[N:18]=[C:17]([N:22]2[CH:26]=[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29](OC(F)(F)F)[CH:28]=3)[N:24]=[CH:23]2)[N:16]=1)[CH2:10][CH:11]([CH3:13])[CH3:12])[CH3:2].[F:39][C:40]([F:46])([F:45])[CH2:41][CH2:42][CH2:43][OH:44].[H-].[Na+].[OH2:49]>CS(C)=O>[CH2:1]([O:3][CH2:4][CH2:5][CH2:6][NH:7][C:8](=[O:38])[CH:9]([NH:14][C:15]1[CH:20]=[C:19]([O:44][CH2:43][CH2:42][CH2:41][C:40]([F:46])([F:45])[F:39])[N:18]=[C:17]([N:22]2[CH:26]=[C:25]([C:27]3[CH:28]=[CH:29][C:30]([O:49][C:40]([F:46])([F:45])[F:39])=[CH:31][CH:32]=3)[N:24]=[CH:23]2)[N:16]=1)[CH2:10][CH:11]([CH3:12])[CH3:13])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1363074,4,4-Trifluorobutan-1-olHCID 865921684-Methyl-2-{6-chloro-2-[4-(3-trifluoromethoxyphenyl)-imidazol-1-yl]-pyrimidin-4-ylamino}-pentanoic acid (3-ethoxypropyl)amide

Product 1

HCID 235687294-Methyl-2-{6-(4,4,4-trifluorobutoxy)-2-[4-(4-trifluoromethoxyphenyl)-imidazol-1-yl]pyrimidin-4-ylamino}pentanoic acid (3-ethoxypropyl) amide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 4-methyl-2-{6-chloro-2-[4-(3-trifluoromethoxyphenyl)-imidazol-1-yl]-pyrimidin-4-ylamino}pentanoic acid (3-ethoxypropyl)amide (145 mg), 4,4,4-trifluoro-1-butanol (135 mg) and NaH (37 mg, 60%) in dimethylsulfoxide (10 ml) was stirred at room temperature for 17 hours. The solution was 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. Semi-preparative HPLC purification provided 16.2 mg of 4-methyl-2-{6-(4,4,4-trifluorobutoxy)-2-[4-(4-trifluoromethoxyphenyl)-imidazol-1-yl]pyrimidin-4-ylamino}pentanoic acid (3-ethoxypropyl) amide. ESI-MS(m/z)647[M+H]+.

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
  6. customSemi-preparative HPLC purification

Sources & evidence

ORD record
ord-3b13eb56bce2424ebe2f9e21ff8c16d0
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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