p-Toluenesulfonic acid monohydrate → 6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine

HRID 1914611노트

반응식

HRID 1914611 반응식
[CH3:1][N:2]1[C:6]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)=[N:5][N:4]=[N:3]1.[NH2:15][O:16][CH2:17][C:18]1[N:23]=[C:22]([NH2:24])[CH:21]=[CH:20][CH:19]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(O)C.ClCCl>[CH3:1][N:2]1[C:6]([C:7](=[N:15][O:16][CH2:17][C:18]2[N:23]=[C:22]([NH2:24])[CH:21]=[CH:20][CH:19]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:5][N:4]=[N:3]1

참가 물질

6

반응물 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 12331986(1-methyl-1H-tetrazol-5-yl)(phenyl)methanoneHCID 450795102-Pyridinamine, 6-[(aminooxy)methyl]-

생성물 1

HCID 768322206-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 6344Dichloromethane용매

반응 조건

온도
160 °C

실험 절차

Under protective gas (argon), a reaction tube containing a solution of (1-methyl-1H-tetrazol-5-yl)(phenyl)methanone (188 mg; 1.0 mmol), 6-[(aminooxy)methyl]pyridin-2-amine (139 mg; 1.0 mmol) and p-toluenesulfonic acid monohydrate (190 mg; 1.0 mmol) in 2-propanol (2 mL) is sealed and heated in a microwave oven at 160° C. for 90 min. For workup, the mixture is allowed to cool down, diluted with dichloromethane (10 mL) and washed twice with 3 ml each time of sat. aq. sodium bicarbonate. The aqueous phase is extracted with dichloromethane and the combined organic layers dried over magnesium sulfate and concentrated under reduced pressure. Purification on silica gel affords 6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-amine as a colourless oil [205 mg; 66% of theory; HPLC/MS: m/z=310 (M+H); log P(HCOOH)=1.13].

후처리

  1. customis sealed
  2. temperatureto cool down
  3. washwashed twice with 3 ml each time of sat. aq. sodium bicarbonate
  4. extractionThe aqueous phase is extracted with dichloromethane
  5. dry with materialthe combined organic layers dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customPurification on silica gel

출처 및 근거

ORD 기록
ord-c6461ee42459420a99264da3e879168d
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08614217B2

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