Triethylamine → HCID 69455767, compound

HRID 2370920Notes

Reaction equation

HRID 2370920 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2[N:16]=[CH:17][NH:18][CH:19]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.Br[CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[CH2:23][CH2:22]1.C(N(CC)CC)C.CC(=O)OCC.O>C1COCC1>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2[N:16]=[CH:17][N:18]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)=[O:28])[CH2:23][CH2:22]3)[CH:19]=2)[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2776275Benzyl 4-bromotetrahydro-1(2H)-pyridinecarboxylateHCID 22728543Water ethylacetateHCID 178470993HCID 178470993, compound

Product 1

HCID 69455767HCID 69455767, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 60.1 mg (0.23 mmol) of the compound from example 1g, 68.9 mg (0.23 mol) of 4-bromo-1-benzyloxycarbonylpiperidine, 97 μl (0.69 mmol) of triethylamine in 1 ml of absolute THF was treated in a microwave at 180° C. for 2 h. The reaction solution was then mixed with 2 ml of EA/water (1:1), and the EA phase was separated off and dried over Na2SO4. Filtering, stripping off the solvent and purifying the remaining residue by chromatography on RP silica gel with CH3CN/water/0.1% TFA as mobile phase afforded 33 mg of the title compound as bistrifluoroacetate.

Workup

  1. customthe EA phase was separated off
  2. dry with materialdried over Na2SO4
  3. filtrationFiltering
  4. custompurifying the remaining residue by chromatography on RP silica gel with CH3CN/water/0.1% TFA as mobile phase

Sources & evidence

ORD record
ord-11efb4951be344c0815461006f9a879d
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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