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

HRID 607429
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HRID 607429 반응식
Br[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([CH3:37])(=[O:36])=[N:10][C:11](=[O:35])[C:12]2[CH:17]=[C:16]([C:18]#[C:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:27]([C:29]4[O:30][CH:31]=[CH:32][C:33]=4[CH3:34])=[O:28])[CH:21]=3)[CH:15]=[N:14][CH:13]=2)=[CH:5][CH:4]=1.[N:38]1([CH2:44][CH2:45][O:46][CH2:47][CH2:48][OH:49])[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1>C1COCC1.CCOC(C)=O>[OH:49][CH2:48][CH2:47][O:46][CH2:45][CH2:44][N:38]1[CH2:43][CH2:42][N:41]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([S:9]([CH3:37])(=[O:36])=[N:10][C:11](=[O:35])[C:12]3[CH:17]=[C:16]([C:18]#[C:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:27]([C:29]5[O:30][CH:31]=[CH:32][C:33]=5[CH3:34])=[O:28])[CH:21]=4)[CH:15]=[N:14][CH:13]=3)=[CH:5][CH:4]=2)[CH2:40][CH2:39]1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 1394361-[2-(2-Hydroxyethoxy)ethyl]piperazineHCID 57657978N-{[4-(Bromomethyl)phenyl] (methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide

생성물 1

HCID 24956708N-{[4-({4-[2-(2-hydroxyethoxy)ethyl]piperazin-1-yl}methyl)phenyl] (methyl)-oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매
HCID 8857
Ethyl Acetate
용매

실험 절차

Crude N-{[4-(Bromomethyl)phenyl] (methyl)oxido--sulfanylidene}-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide was dissolved in THF (2 mL). 2-(2-piperazin-1-yl-ethoxy)-ethanol (0.064 g, 0.390 mmol) and TEA (0.054 mL, 0.390 mmol) were then added to the solution and the resulting reaction mixture was allowed to stir for 1 h at rt. The reaction mixture, subsequently, was dissolved in EtOAc and then extracted with H2O (2× mL). The organic layer was dried over anhydrous Na2SO4(s), filtered and concentrated in vacuo. The crude product was purified via column chromatography (gradient eluant mixture of MeOH in EtOAc: 0% to 20% MeOH) to afford the title compound (0.064 g, 49% overall for step 1 and 2).

후처리

  1. customthe resulting reaction mixture
  2. extractionextracted with H2O (2× mL)
  3. dry with materialThe organic layer was dried over anhydrous Na2SO4(s)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified via column chromatography (gradient eluant mixture of MeOH in EtOAc: 0% to 20% MeOH)

출처 및 근거

ORD 기록
ord-0520d9cee8d64c1b873e6702e9ca0209
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07915443B2

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