HCID 58588457, compound → HCID 58588477, compound

HRID 1361706Notes

Reaction equation

HRID 1361706 reaction equation
[CH3:1][N:2]([CH3:37])[CH2:3][C:4]#[C:5][C:6]1[CH:7]=[C:8]([CH:34]=[CH:35][CH:36]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][CH3:32])[N:26]=3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[C:14]([CH3:33])[CH:13]=1)=[O:10].[H][H]>CCO.[Pd]>[CH3:37][N:2]([CH3:1])[CH2:3][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([CH:34]=[CH:35][CH:36]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([C:25]3[CH:30]=[CH:29][N:28]=[C:27]([NH:31][CH3:32])[N:26]=3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[C:14]([CH3:33])[CH:13]=1)=[O:10]

Participants

5

Reactant 2

HCID 58588457HCID 58588457, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 58588477HCID 58588477, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent2×

Procedure

To a mixture of 3-(3-(dimethylamino)prop-1-ynyl)-N-(3-methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)benzamide (0.060 g, 0.12 mmol) in EtOH (4 mL) was added a suspension of 10% Pd/C (0.012 g, 0.012 mmol) in ethanol. The reaction was exposed to approximately 30 psi hydrogen and was shaken in a Parr apparatus for 5 h. The reaction was filtered through celite, and the filtrate was concentrated in vacuo. The resulting yellow oil was purified by reverse-phase HPLC using acetonitrile/water/TFA to give 3-(3-(dimethylamino)propyl)-N-(3-methyl-4-(3-(2-(methylamino)pyrimidin-4-yl)pyridin-2-yloxy)phenyl)benzamide as an off-white solid. MS m/z=497 [M+1]+. Calc'd for C29H32N6O2: 496.61.

Workup

  1. additionwas added
  2. filtrationThe reaction was filtered through celite
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe resulting yellow oil was purified by reverse-phase

Sources & evidence

ORD record
ord-e83289b3ac4744868c88a668e05e0512
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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