Potassium Carbonate → HCID 86626898, compound

HRID 604158Notes

Reaction equation

HRID 604158 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:46][CH3:47])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2[CH2:20][N:21]([CH2:34][C:35]2[CH:36]=[C:37]([OH:45])[CH:38]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:40]=2)[C:22]2[N:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:24][N:23]=2)[CH:9]=1)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:55][CH2:56][CH2:57][C:58]([O:60][CH2:61][CH3:62])=[O:59]>CN(C)C=O.[Cl-].[Na+].O>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([O:46][CH3:47])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][C:11]=2[CH2:20][N:21]([CH2:34][C:35]2[CH:36]=[C:37]([CH:38]=[C:39]([C:41]([F:44])([F:42])[F:43])[CH:40]=2)[O:45][CH2:55][CH2:56][CH2:57][C:58]([O:60][CH2:61][CH3:62])=[O:59])[C:22]2[N:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:24][N:23]=2)[CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 76300Ethyl 4-bromobutyrateHCID 86626897HCID 86626897, compound

Product 1

HCID 86626898HCID 86626898, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

3-{[(5′-Isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-methyl}-5-trifluoromethyl-phenol (95 mg) is dissolved in N,N-dimethylformamide (1 ml), and thereto are added potassium carbonate (90 mg) and ethyl 4-bromobutyrate (93 μl) and the mixture is stirred at room temperature for 4 hours. To the reaction mixture is added a saturated brine, and the mixture is extracted with ethyl acetate, and the organic layer is washed with a saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=10:1→4:1) to give ethyl 4-(3-{[(5′-isopropyl-2′-methoxy-4-trifluoromethyl-biphenyl-2-ylmethyl)-(5-morpholin-4-yl-pyrimidin-2-yl)-amino]-methyl}-5-trifluoromethyl-phenoxy)butyrate (92 mg). MS (m/z): 775 [M+H]+

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washthe organic layer is washed with a saturated brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by silica gel column chromatography (hexane:ethyl acetate=10:1→4:1)

Sources & evidence

ORD record
ord-a112e0536ddc436fa6e0dd36d98ba6cc
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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