1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 3-{[6-(acetylamino)pyridin-3-yl]ethynyl}-4-methyl-N-{4-[(4-methylpiperazin-1-yl)methyl]-3-(trimethylsilyl)phenyl}benzamide

HRID 1527896Notes

Reaction equation

HRID 1527896 reaction equation
[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:16]([OH:18])=O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[CH3:23][N:24]1[CH2:29][CH2:28][N:27]([CH2:30][C:31]2[CH:37]=[CH:36][C:34]([NH2:35])=[CH:33][C:32]=2[Si:38]([CH3:41])([CH3:40])[CH3:39])[CH2:26][CH2:25]1.CCN=C=NCCCN(C)C>N1C=CC=CC=1>[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8]([C:11]#[C:12][C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:16]([NH:35][C:34]2[CH:36]=[CH:37][C:31]([CH2:30][N:27]3[CH2:26][CH2:25][N:24]([CH3:23])[CH2:29][CH2:28]3)=[C:32]([Si:38]([CH3:39])([CH3:41])[CH3:40])[CH:33]=2)=[O:18])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 577751104-(4-Methylpiperazin-1-ylmethyl)-3-trimethylsilylanilineHCID 68899408HCID 68899408, compound

Product 1

HCID 577752213-{[6-(acetylamino)pyridin-3-yl]ethynyl}-4-methyl-N-{4-[(4-methylpiperazin-1-yl)methyl]-3-(trimethylsilyl)phenyl}benzamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-{[6-(acetylamino)pyridin-3-yl]ethynyl}-4-methylbenzoic acid (0.22 mmol) in dry pyridine (5 mL) is added 4-(4-methylpiperazin-1-ylmethyl)-3-trimethylsilylaniline (60 mg, 0.22 mmol) and EDCI (62 mg, 0.325 mmol). The resulting mixture is stirred at r.t. overnight. The solvent is removed on rotavap and the residue is partitioned between DCM and aq. NaHCO3. The combined organic layers from extraction are dried (Na2SO4), filtered, concentrated, and the resulting residue is purified by silica gel flash chromatography [eluted with 5% MeOH (pre-saturated with NH3) in DCM] to give the desired product.

Workup

  1. customThe solvent is removed on rotavap
  2. customthe residue is partitioned between DCM and aq. NaHCO3
  3. extractionThe combined organic layers from extraction
  4. dry with materialare dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customthe resulting residue is purified by silica gel flash chromatography [eluted with 5% MeOH (pre-saturated with NH3) in DCM]

Sources & evidence

ORD record
ord-45bac536ba194f288347d702a390dc51
Source dataset
uspto-grants-2015_07
Patent number
US09090561B2

Reaction notes

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