Potassium Hydroxide → 6-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-amine

HRID 1042338노트

반응식

HRID 1042338 반응식
CC(C)(C)C([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH:12]([O:14][N:15]=[C:16]([C:23]2[N:27]([CH3:28])[N:26]=[N:25][N:24]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH3:13])[N:7]=1)=O.[OH-].[K+]>C(O)C>[CH3:28][N:27]1[C:23]([C:16](=[N:15][O:14][CH:12]([C:8]2[N:7]=[C:6]([NH2:5])[CH:11]=[CH:10][CH:9]=2)[CH3:13])[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)=[N:24][N:25]=[N:26]1

참가 물질

4

반응물 2

HCID 14797Potassium HydroxideHCID 866499712,2-dimethyl-N-{6-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-yl}propanamide

생성물 1

HCID 866499726-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-amine수율 68.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a stirred solution of 2,2-dimethyl-N-{6-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-yl}propanamide (19.7 g, 48.3 mmol, 1 eq.) in 200 ml of ethanol, was added potassium hydroxide (88.4 g, 1.57 mol, 32.6 eq.). The reaction mixture was stirred and heated to reflux for 4 hrs. After evaporation of the solvent, The residue was taken up with water (300 ml) and extracted with EtOAc (100 ml). The aqueous layer was separated and extracted twice with EtOAc (100 ml). The organics were combined, dried over MgSO4 and concentrated. The crude material was purified by chromatography on silica gel to give 6-[1-({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)ethyl]pyridin-2-amine (10.7 g, 90% pure, 61% yield)

후처리

  1. temperatureheated
  2. temperatureto reflux for 4 hrs
  3. customAfter evaporation of the solvent
  4. extractionextracted with EtOAc (100 ml)
  5. customThe aqueous layer was separated
  6. extractionextracted twice with EtOAc (100 ml)
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated
  9. customThe crude material was purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-b9009fd8fd864abc8c0e1bd9efb1f714
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557849B2

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