Ethyl Acetate → Ethyl 4-(2-{(3-cyano-5-trifluoromethyl-benzyl)-[2-(cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-5-yloxy)-butyrate

HRID 604089Notes

Reaction equation

HRID 604089 reaction equation
C([C:3]1[C:10]([CH2:11][N:12]([CH2:20][C:21]2[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][C:22]=2[N:31]([CH2:35][CH:36]2[CH2:38][CH2:37]2)[CH2:32][CH2:33][CH3:34])[C:13]2[N:18]=[CH:17][C:16]([OH:19])=[CH:15][N:14]=2)=[CH:9][C:8]([C:39]([F:42])([F:41])[F:40])=[CH:7][C:4]=1[C:5]#[N:6])C.Br[CH2:44][CH2:45][CH2:46][C:47]([O-:49])=[O:48].C(=O)([O-])[O-].[K+].[K+].[C:56](OCC)(=O)[CH3:57]>CN(C)C=O>[C:5]([C:4]1[CH:3]=[C:10]([CH:9]=[C:8]([C:39]([F:41])([F:40])[F:42])[CH:7]=1)[CH2:11][N:12]([CH2:20][C:21]1[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=[CH:23][C:22]=1[N:31]([CH2:35][CH:36]1[CH2:37][CH2:38]1)[CH2:32][CH2:33][CH3:34])[C:13]1[N:18]=[CH:17][C:16]([O:19][CH2:44][CH2:45][CH2:46][C:47]([O:49][CH2:56][CH3:57])=[O:48])=[CH:15][N:14]=1)#[N:6]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 69936583-BromomethylpropionateHCID 86626843Ethyl 3-{[[2-(cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzyl]-(5-hydroxy-pyrimidin-2-yl)-amino]-methyl}-5-trifluoromethyl-benzonitrile

Product 1

HCID 86626842Ethyl 4-(2-{(3-cyano-5-trifluoromethyl-benzyl)-[2-(cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-5-yloxy)-butyrate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Ethyl 3-{[[2-(cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzyl]-(5-hydroxy-pyrimidin-2-yl)-amino]-methyl}-5-trifluoromethyl-benzonitrile (250 mg) and 4-bromobutyrate (76.9 μl) is dissolved in N,N-dimethylformamide (3.7 ml) and thereto is added potassium carbonate (74 mg) and the mixture is stirred at room temperature overnight. Thereto are added ethyl acetate and a saturated brine, and the mixture is separated, and the organic layer is washed with a saturated brine, dried and concentrated under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (hexane:ethyl acetate=8:1) to give ethyl 4-(2-{(3-cyano-5-trifluoromethyl-benzyl)-[2-(cyclopropylmethyl-propyl-amino)-5-trifluoromethyl-benzyl]-amino}-pyrimidin-5-yloxy)-butyrate (220 mg). MS (m/z): 678 [M+H]+

Workup

  1. customa saturated brine, and the mixture is separated
  2. washthe organic layer is washed with a saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue is purified by NH-silica gel column chromatography (hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-25af1e3999f24f72930763c776ca550b
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

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