Triethylamine → HCID 57709115, compound

HRID 547154Notes

Reaction equation

HRID 547154 reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][C:11](=[O:54])[CH2:12][C:13]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([C:30]3[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][CH:38]([O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45])[C:39]([CH3:42])([CH3:41])[CH3:40])=[C:32]([CH3:51])[CH:31]=3)([CH2:28][CH3:29])[CH2:26][CH3:27])=[CH:21][C:20]=2[CH3:52])[N:16]=[N:15][C:14]=1Cl)[CH3:9].[H][H]>C(O)C.C(OCC)C.[Pd]>[CH2:8]([O:10][C:11](=[O:54])[CH2:12][C:13]1[CH:18]=[C:17]([C:19]2[CH:24]=[CH:23][C:22]([C:25]([C:30]3[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][CH:38]([O:43][Si:44]([C:47]([CH3:50])([CH3:49])[CH3:48])([CH3:46])[CH3:45])[C:39]([CH3:42])([CH3:41])[CH3:40])=[C:32]([CH3:51])[CH:31]=3)([CH2:26][CH3:27])[CH2:28][CH3:29])=[CH:21][C:20]=2[CH3:52])[N:16]=[N:15][CH:14]=1)[CH3:9]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 57709054HCID 57709054, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 57709115HCID 57709115, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

10% Pd-C (2 mg) and triethylamine (0.011 mL, 0.079 mmol) were added to a solution of {6-[4-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-3-chloro-pyridazin-4-yl}acetic acid ethyl ester (Example 183-(2); 4.8 mg, 0.007 mmol) in ethanol (0.6 mL) at room temperature. After replacement with hydrogen, the mixture was stirred in a hydrogen atmosphere at room temperature for seven hours. The reaction mixture was diluted with diethyl ether and filtered. The filtrate was washed with water, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1) to give the title compound (3.7 mg, 82%).

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-ac7958df379746459b295b9b3e59caff
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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