1-[2-(2-Hydroxyethoxy)ethyl]piperazine → (S)-N-[(3-{4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl}propyl)(oxido)phenyl--sulfanylidene]-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide

HRID 607451

Reaction equation

HRID 607451 reaction equation
Br[CH2:2][CH2:3][CH2:4][S:5](=[O:38])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[N:6][C:7](=[O:31])[C:8]1[CH:13]=[C:12]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([C:25]3[O:26][CH:27]=[CH:28][C:29]=3[CH3:30])=[O:24])[CH:17]=2)[CH:11]=[N:10][CH:9]=1.[OH:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][N:45]1[CH2:50][CH2:49][NH:48][CH2:47][CH2:46]1>CN(C=O)C>[OH:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][N:45]1[CH2:50][CH2:49][N:48]([CH2:2][CH2:3][CH2:4][S@:5](=[O:38])([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[N:6][C:7](=[O:31])[C:8]2[CH:13]=[C:12]([C:14]#[C:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23]([C:25]4[O:26][CH:27]=[CH:28][C:29]=4[CH3:30])=[O:24])[CH:17]=3)[CH:11]=[N:10][CH:9]=2)[CH2:47][CH2:46]1

Participants

4

Reactant 2

HCID 1394361-[2-(2-Hydroxyethoxy)ethyl]piperazineHCID 76585264N-[(3-bromopropyl)(oxido)phenyl--sulfanylidene]-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide

Product 1

HCID 46242011(S)-N-[(3-{4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl}propyl)(oxido)phenyl--sulfanylidene]-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To the solution of N-[(3-bromopropyl)(oxido)phenyl--sulfanylidene]-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide (450 mg, 0.76 mmol) in anhydrous DMF (5 mL) was added dropwise 1-[2-(2-hydroxyethoxy)ethyl]piperazine. The resulting reaction solution was stirred and heated at 80° C. for 30 min. It was then partitioned between saturated aqueous NaHCO3 and EtOAc. The EtOAc layer was separated and washed with brine (1×). The aqueous NaHCO3 layer was extracted with CHCl3 (1×) and the extract was washed with brine (1×). The organic layers were combined and dried over anhydrous sodium sulfate. The organic solution was decanted, concentrated, and wrapped with silica gel. Column chromatography (MeOH-EtOAc from 1:10 to 1:6) rendered the title compound as white foam in amount of 500 mg (96%).

Workup

  1. customThe resulting reaction solution
  2. customIt was then partitioned between saturated aqueous NaHCO3 and EtOAc
  3. customThe EtOAc layer was separated
  4. washwashed with brine (1×)
  5. extractionThe aqueous NaHCO3 layer was extracted with CHCl3 (1×)
  6. washthe extract was washed with brine (1×)
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe organic solution was decanted
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-a5f58b26d79f44ed82e0b6ec818e5f39
Source dataset
uspto-grants-2011_03
Patent number
US07915443B2

Linked notes

Loading…