Sodium hydride → 3-[5-(2-Fluoro-phenyl)-pyridin-2-yloxy]-azetidine-1-carboxylic acid pyridazin-4-ylamide

HRID 1469387ノート

反応式

HRID 1469387 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][N:2]=1.[H-].[Na+].[N+](C1C=CC([O:19][C:20]([N:22]2[CH2:25][CH:24]([O:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[F:39])=[CH:29][N:28]=3)[CH2:23]2)=O)=CC=1)([O-])=O>CN(C=O)C>[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:20]([N:22]2[CH2:23][CH:24]([O:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=4[F:39])=[CH:29][N:28]=3)[CH2:25]2)=[O:19])=[CH:3][N:2]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 2984924-AminopyridazineHCID 580731093-[5-(2-Fluoro-phenyl)-pyridin-2-yloxy]-azetidine-1-carboxylic acid 4-nitro-phenyl ester

生成物 1

HCID 442192143-[5-(2-Fluoro-phenyl)-pyridin-2-yloxy]-azetidine-1-carboxylic acid pyridazin-4-ylamide収率 16%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a solution of Pyridazin-4-ylamine (30 mg, 0.31 mmol, [Cas. No. 20744-39-2]) in DMF (3 mL) at 0° C. was added sodium hydride (20 mg, 0.5 mmol, 60% disp. in mineral oil). After stirring at 0° C. for 15 min. a solution of 3-[5-(2-Fluoro-phenyl)-pyridin-2-yloxy]-azetidine-1-carboxylic acid 4-nitro-phenyl ester (102 mg, 0.25 mmol) in DMF (4 mL) was added dropwise. After stirring for 16 hrs at ambient temperature the reaction mixture was concentrated in vacuo, diluted with ethyl acetate (50 mL) and washed sequentially with sat. aqueous sodium hydrogen carbonate solution (2×50 mL) then sat. sodium chloride solution (50 mL). Mixture dried over magnesium sulphate and filtered. Filtrate solvents were removed in vacuo and the residue was purified by preparative HPLC to give the title compound (15 mg, 16%)

後処理

  1. additionwas added dropwise
  2. concentrationwas concentrated in vacuo
  3. additiondiluted with ethyl acetate (50 mL)
  4. washwashed sequentially with sat. aqueous sodium hydrogen carbonate solution (2×50 mL)
  5. dry with materialMixture dried over magnesium sulphate
  6. filtrationfiltered
  7. customFiltrate solvents were removed in vacuo
  8. customthe residue was purified by preparative HPLC

出典と根拠

ORDレコード
ord-29cb4a31d59d4ed49f01f62c1cfaf580
出典データセット
uspto-grants-2015_04
特許番号
US09006269B2

反応ノート

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