Acetonitrile → 7-[2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazol-3-yl]-5-methyl-1H-8-oxa-1,2,6-triaza-cyclopenta[a]naphthalen-9-one

HRID 1907135ノート

反応式

HRID 1907135 の反応式
[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]([OH:15])=O)=[CH:11][C:10]([O:16][CH3:17])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.C(#N)C.[NH2:21][C:22]1[C:30]([C:31](O)=[O:32])=[C:29]2[C:25]([CH:26]=[N:27][NH:28]2)=[CH:24][C:23]=1[CH3:34].S(Cl)(C)(=O)=O>N1C=CC=CC=1>[Cl:1][C:2]1[C:3]([N:8]2[C:12]([C:13]3[O:15][C:31](=[O:32])[C:30]4[C:29]5[NH:28][N:27]=[CH:26][C:25]=5[CH:24]=[C:23]([CH3:34])[C:22]=4[N:21]=3)=[CH:11][C:10]([O:16][CH3:17])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 6342AcetonitrileHCID 31297Methanesulfonyl chlorideHCID 468557186-amino-5-methyl-2H-indazole-7-carboxylic acidHCID 509892861-(3-chloropyridin-2-yl)-3-methoxy-1H-pyrazole-5-carboxylic acid

生成物 1

HCID 579901547-[2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazol-3-yl]-5-methyl-1H-8-oxa-1,2,6-triaza-cyclopenta[a]naphthalen-9-one

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
50 °C

実験手順

To a solution of 2-(3-chloro-pyridin-2-yl)-5-methoxy-2H-pyrazole-3-carboxylic acid (40 g, 157 mmol) and acetonitrile (1000 mL) was added 6-amino-5-methyl-1H-indazole-7-carboxylic acid (30 g, 157 mmol). To the resulting brown suspension were added sequentially pyridine (57 mL, 706 mml) and dropwise mesylchloride (43 mL, 549 mmol). The reaction mixture was stirred for 6 h at 50° C. and 15 hours at ambient temperature. The reaction mixture was concentrated in vacuo. The residue was suspended in water and stirred for 15 min. The resulting yellow suspension was filtrated. The filtercake was washed sequentially with water and heptane/AcOEt 2:1 and dried to afford the title compound as beige powder, which was submitted to the next step without further purification. LC/MS: 409 (M+H)+.

後処理

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. stirringstirred for 15 min
  3. filtrationThe resulting yellow suspension was filtrated
  4. washThe filtercake was washed sequentially with water and heptane/AcOEt 2:1
  5. customdried

出典と根拠

ORDレコード
ord-e8ce601b35ef4954bb8c07a72de8d625
出典データセット
uspto-grants-2013_12
特許番号
US08598078B2

反応ノート

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