N,N-Dimethylpropargylamine → HCID 58588457, compound

HRID 446348Notes

Reaction equation

HRID 446348 reaction equation
I[C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:27][CH3:28])[N:22]=3)=[CH:19][CH:18]=[CH:17][N:16]=2)=[C:10]([CH3:29])[CH:9]=1)=[O:6].[CH3:33][N:34]([CH3:38])[CH2:35][C:36]#[CH:37]>C(N(CC)CC)C.C(#N)C.ClCCl.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:33][N:34]([CH3:38])[CH2:35][C:36]#[C:37][C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][C:15]2[C:20]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([NH:27][CH3:28])[N:22]=3)=[CH:19][CH:18]=[CH:17][N:16]=2)=[C:10]([CH3:29])[CH:9]=1)=[O:6]

Participants

8

Reactant 2

HCID 81643N,N-DimethylpropargylamineHCID 66970357HCID 66970357, compound

Product 1

HCID 58588457HCID 58588457, compound

Reagents, catalysts & solvents 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178419050HCID 178419050, compoundCatalystHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

A mixture of 3-iodo-N-(3-methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)benzamide (0.20 g, 0.37 mmol), N,N-dimethylprop-2-yn-1-amine (0.080 mL, 0.74 mmol), bis(triphenylphosphine)palladium (II) dichloride (0.013 g, 0.020 mmol), copper (I) iodide (0.0035 g, 0.020 mmol) in triethylamine (1.5 mL) and acetonitrile (5 mL) was heated in a sealed tube to 100 deg. C. for 3.5 h. The reaction was diluted in dichloromethane and filtered. The filtrate was concentrated in vacuo and the resulting material was purified by silica gel chromatography using MeOH/dichloromethane as eluent to give 3-(3-(dimethylamino)prop-1-ynyl)-N-(3-methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)benzamide as a brown solid. MS m/z=493 [M+1]+. Calc'd for C29H28N6O2: 492.58.

Workup

  1. temperaturewas heated in a sealed tube to 100 deg. C
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe resulting material was purified by silica gel chromatography

Sources & evidence

ORD record
ord-b2ae6dd547f940a38b43a195f2c8a06f
Source dataset
uspto-grants-2013_07
Patent number
US08476434B2

Reaction notes

Loading…