Ethyl 4-piperidinecarboxylate → HCID 86626782, compound

HRID 604023Notes

Reaction equation

HRID 604023 reaction equation
[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][N:7]([C:22]1[N:27]=[CH:26][C:25](Br)=[CH:24][N:23]=1)[CH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1[O:19][CH2:20][CH3:21].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+].[NH:65]1[CH2:70][CH2:69][CH:68]([C:71]([O:73][CH2:74][CH3:75])=[O:72])[CH2:67][CH2:66]1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C>[F:1][C:2]([F:37])([F:36])[C:3]1[CH:4]=[C:5]([CH:29]=[C:30]([C:32]([F:35])([F:34])[F:33])[CH:31]=1)[CH2:6][N:7]([CH2:8][C:9]1[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:12]=[CH:11][C:10]=1[O:19][CH2:20][CH3:21])[C:22]1[N:27]=[CH:26][C:25]([N:65]2[CH2:70][CH2:69][CH:68]([C:71]([O:73][CH2:74][CH3:75])=[O:72])[CH2:67][CH2:66]2)=[CH:24][N:23]=1

Participants

9

Reactant 5

HCID 70770Ethyl 4-piperidinecarboxylateHCID 516892Sodium BicarbonateHCID 27342152-(Di-tert-butylphosphino)biphenylHCID 23676156Sodium t-butoxideHCID 86626781(3,5-Bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-(2-ethoxy-5-trifluoromethyl-benzyl)-amine

Product 1

HCID 86626782HCID 86626782, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

(3,5-Bis-trifluoromethyl-benzyl)-(5-bromo-pyrimidin-2-yl)-(2-ethoxy-5-trifluoromethyl-benzyl)-amine (210 mg) is dissolved in toluene (5 ml) and thereto are added tris(dibenzylideneacetone)dipalladium (32 mg), 2-(di-tert-butylphosphino)biphenyl (42 mg), sodium tert-butoxide (50 mg) and ethyl piperidine-4-carboxylate (80 μl) and the mixture is stirred under nitrogen atmosphere at room temperature overnight. To the reaction solution are added a saturated aqueous sodium bicarbonate solution and ethyl acetate, and the mixture is separated, 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 NH-silica gel column chromatography (hexane:ethyl acetate=1:0→17:3) to give ethyl 1-{2-[(3,5-bis-trifluoromethyl-benzyl)-(2-ethoxy-5-trifluoromethyl-benzyl)-amino]-pyrimidin-5-yl}-piperidine-4-carboxylate (121 mg). MS (m/z): 679 [M+H]+

Workup

  1. customthe mixture is separated
  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 NH-silica gel column chromatography (hexane:ethyl acetate=1:0→17:3)

Sources & evidence

ORD record
ord-f4feaf8535734ce5bf1c66b20807ca84
Source dataset
uspto-grants-2011_03
Patent number
US07906517B2

Reaction notes

Loading…