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

HRID 1914611

反応式

HRID 1914611 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
160 °C

実験手順

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].

後処理

  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

出典と根拠

ORDレコード
ord-c6461ee42459420a99264da3e879168d
出典データセット
uspto-grants-2013_12
特許番号
US08614217B2

関連ノート

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