Dimethylformamide → HCID 86731564, compound

HRID 1430580Notes

Reaction equation

HRID 1430580 reaction equation
[C:1]([C@@H:3]1[CH2:8][N:7]([C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[N:17]2[N:21]=[CH:20][CH:19]=[N:18]2)=[O:10])[C@H:6]([CH3:22])[CH2:5][CH2:4]1)#[CH:2].C([N:25]([CH2:28][CH3:29])[CH2:26][CH3:27])C.[CH3:30]N(C=O)C>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:22][C@@H:6]1[CH2:5][CH2:4][C@H:3]([C:1]#[C:2][C:28]2[CH:29]=[CH:30][CH:27]=[CH:26][N:25]=2)[CH2:8][N:7]1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N:17]1[N:21]=[CH:20][CH:19]=[N:18]1)=[O:10]

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 86731565HCID 86731565, compound

Product 1

HCID 86731564HCID 86731564, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

To a solution of [(2R,5R)-5-ethynyl-2-methylpiperidin-1-yl][2-(2H-1,2,3-triazol-2-yl)phenyl]methanone (0.015 g, 0.051 mmol) in DMF (0.5 mL) under an atmosphere of nitrogen was added triethylamine (0.071 mL, 0.51 mmol), copper(I) iodide (2.9 mg, 0.015 mmol), and palladium tetrakis (5.9 mg, 0.0051 mmol). The reaction was heated to 100° C. for 17 h, then cooled to RT. Excess QuadraPure TU was added, and after 1 h, the solids were removed via filtration. The solution was subjected to purification via reverse phase HPLC to provide the [(2R,5R)-2-methyl-5-(pyridin-2-ylethynyl)piperidin-1-yl][2-(2H-1,2,3-triazol-2-yl)phenyl]methanone which gave a high resolution mass spectrum (ES+) m/z of 372.1812, calculated for M+H+ [C22H21N5O: 372.1819].

Workup

  1. temperaturecooled to RT
  2. additionExcess QuadraPure TU was added
  3. customthe solids were removed via filtration
  4. customThe solution was subjected to purification via reverse phase HPLC

Sources & evidence

ORD record
ord-adbd28901e63467781d68b797039e9d3
Source dataset
uspto-grants-2015_01
Patent number
US08940898B2

Reaction notes

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