N,N-Dimethylpropargylamine → HCID 20773385, compound

HRID 1815197Notes

Reaction equation

HRID 1815197 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([C:14]2[C:15]([NH:20][CH2:21][C:22]3[CH:27]=[CH:26][N:25]=[C:24](Cl)[CH:23]=3)=[N:16][CH:17]=[CH:18][CH:19]=2)=[O:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:29][N:30]([CH3:34])[CH2:31][C:32]#[CH:33]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:29][N:30]([CH3:34])[CH2:31][C:32]#[C:33][C:24]1[CH:23]=[C:22]([CH2:21][NH:20][C:15]2[C:14]([C:12]([NH:11][C:8]3[CH:9]=[CH:10][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=3)=[O:13])=[CH:19][CH:18]=[CH:17][N:16]=2)[CH:27]=[CH:26][N:25]=1

Participants

5

Reactant 2

HCID 81643N,N-DimethylpropargylamineHCID 22249455HCID 22249455, compound

Product 1

HCID 20773385HCID 20773385, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of N-[4-(tert-butyl)phenyl](2-{[(2-chloro(4-pyridyl))methyl]amino}(3-pyridyl))carboxamide (0.15 g, 0.38 mmol, Example 139), 1-dimethylamino-2-propyne (62 mg, 0.76 mmol), PdCl2(PPh3)2 (13 mg, 0.0019 mmol) and CuI (7 mg, 0.019 mmol) in 1 mL of TEA was heated at 100° C. in a sealed tube for 3 h. The resulting mixture was filtered over Celite®. The filtrate was concentrated, and the residue was purified by prep-HPLC (reverse phase) to give the title compound. MS (ES+): 442 (M+H)+; (ES−): 440(M−H)−. Calc'd C27H31N5O—441.58.

Workup

  1. filtrationThe resulting mixture was filtered over Celite®
  2. concentrationThe filtrate was concentrated
  3. customthe residue was purified by prep-HPLC (reverse phase)

Sources & evidence

ORD record
ord-a7504c35936e426aad9eb398dd638876
Source dataset
uspto-grants-2005_04
Patent number
US06878714B2

Reaction notes

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