3-(Methylamino)propane-1,2-diol → N-[{2-[(2,3-dihydroxypropyl)(methyl)amino]-2-oxoethyl}(oxido)phenyl--sulfanylidene]-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide

HRID 607470노트

반응식

HRID 607470 반응식
C([C@H:3]([S:7]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)(=[N:9][C:10]([C:12]1[CH:13]=[N:14][CH:15]=[C:16]([C:18]#[C:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:27]([C:29]3[O:30][CH:31]=[CH:32][C:33]=3[CH3:34])=[O:28])[CH:21]=2)[CH:17]=1)=[O:11])=[O:8])[C:4]([O-])=[O:5])C.[CH3:41][NH:42][CH2:43][CH:44]([OH:47])[CH2:45][OH:46]>C1COCC1>[OH:47][CH:44]([CH2:45][OH:46])[CH2:43][N:42]([CH3:41])[C:4](=[O:5])[CH2:3][S:7](=[O:8])([C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)=[N:9][C:10](=[O:11])[C:12]1[CH:17]=[C:16]([C:18]#[C:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([NH:26][C:27]([C:29]3[O:30][CH:31]=[CH:32][C:33]=3[CH3:34])=[O:28])[CH:21]=2)[CH:15]=[N:14][CH:13]=1

참가 물질

4

반응물 2

HCID 27341223-(Methylamino)propane-1,2-diolHCID 86629488(S)-ethyl(N-{[5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)pyridin-3-yl]carbonyl}-S-phenylsulfonimidoyl)acetate

생성물 1

HCID 57657936N-[{2-[(2,3-dihydroxypropyl)(methyl)amino]-2-oxoethyl}(oxido)phenyl--sulfanylidene]-5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)nicotinamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
75 °C

실험 절차

To the solution of (S)-ethyl(N-{[5-({3-[(3-methyl-2-furoyl)amino]phenyl}ethynyl)pyridin-3-yl]carbonyl}-S-phenylsulfonimidoyl)acetate (3.5 g, 6.3 mmol) in anhydrous THF (50 mL) was added dropwise 3-methylamino-1,2-propanediol (6.77 g) and the resulting reaction solution was heated at 75° C. for 8.5 hours. The reaction was then concentrated under reduced pressure and the yellow oily residue was partitioned between aqueous NH4Cl and EtOAc. The organic layer was separated and washed with saturated aqueous NaHCO3 (1×), brine (1×), and dried with sodium sulfate. The upper clear solution was decanted and evaporated, the resulting yellowish foamy residue was subjected to a gradient column chromatography (from EtOAc-Hex 6:1 to MeOH-EtOAc 1:50) yielding the title compound as white foam in amount of 2.56 g (66%).

후처리

  1. customthe resulting reaction solution
  2. concentrationThe reaction was then concentrated under reduced pressure
  3. customthe yellow oily residue was partitioned between aqueous NH4Cl and EtOAc
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous NaHCO3 (1×), brine (1×)
  6. dry with materialdried with sodium sulfate
  7. customThe upper clear solution was decanted
  8. customevaporated

출처 및 근거

ORD 기록
ord-5a7f2b452674402482697f3639fafae1
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07915443B2

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