1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 3-{[6-(acetylamino)pyridin-3-yl]ethynyl}-4-methyl-N-{4-[(4-methylpiperazin-1-yl)methyl]-3-(trimethylsilyl)phenyl}benzamide

HRID 1255961Notes

Reaction equation

HRID 1255961 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.Cl>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 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 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 EDCl (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-42353efa4ab144a9b16423e921467c33
Source dataset
uspto-grants-2013_06
Patent number
US08461167B2

Reaction notes

Loading…