Triethylamine → HCID 68505362, compound

HRID 1176399Notes

Reaction equation

HRID 1176399 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[C:8]([O:15][CH2:16][CH2:17][O:18][CH:19]2[CH:24]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[O:43][CH3:44])=[CH:27][CH:26]=3)[CH2:23][CH2:22][N:21]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:20]2)=[N:9][C:10]([CH3:14])=[N:11][C:12]=1Cl)(=[O:3])[CH3:2].C(N(CC)CC)C>C(O)C.[Pd]>[C:1]([NH:4][CH2:5][CH2:6][C:7]1[C:8]([O:15][CH2:16][CH2:17][O:18][CH:19]2[CH:24]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][CH2:34][O:35][CH2:36][C:37]4[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=4[O:43][CH3:44])=[CH:27][CH:26]=3)[CH2:23][CH2:22][N:21]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:20]2)=[N:9][C:10]([CH3:14])=[N:11][CH:12]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 8471TriethylamineHCID 86610002HCID 86610002, compound

Product 1

HCID 68505362HCID 68505362, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 0.191 g of tert-butyl 3-{2-[5-(2-acetylaminoethyl)-6-chloro-2-methylpyrimidin-4-yloxy]ethoxy}-4-{4-[3-(2-methoxybenzyloxy)propoxy]phenyl}piperidine-1-carboxylate and 0.055 ml of triethylamine in 6 ml of ethanol is hydrogenated in the presence of 0.060 g of 10% Pd/C (added 4 times) at room temperature over 60 hours. The reaction mixture is clarified by filtration and the filtrate is concentrated by evaporation. The residue is taken up in ethyl acetate, washed with water and brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.22 (95:5 dichloromethane-methanol); Rt=4.54.

Workup

  1. filtrationThe reaction mixture is clarified by filtration
  2. concentrationthe filtrate is concentrated by evaporation
  3. washwashed with water and brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-1443d460065441af8bdaaaccb0b81f65
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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