Picolinic acid → Pyridine-2-carboxylic acid-(4-(1-acetyl-pyrrolidin-2-yl)-3-fluoro-phenyl)-amide

HRID 13355

反応式

HRID 13355 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=O.Cl.[CH3:11]N(C)CCCN=C=NCC.[NH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]2[CH2:33][CH2:32][CH2:31][N:30]2[C:34](OC(C)(C)C)=[O:35])=[C:25]([F:41])[CH:24]=1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.N1C=CC=CC=1>[C:34]([N:30]1[CH2:31][CH2:32][CH2:33][CH:29]1[C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[O:9])=[CH:24][C:25]=1[F:41])(=[O:35])[CH3:11]

参加物

7

反応物 4

HCID 1018Picolinic acidHCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 23145592t-Butyl 2-(4-amino-2-fluoro-phenyl)-pyrrolidine-1-carboxylate

生成物 1

HCID 23145364Pyridine-2-carboxylic acid-(4-(1-acetyl-pyrrolidin-2-yl)-3-fluoro-phenyl)-amide

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6212Chloroform溶媒3 回

実験手順

90 mg of pyridine-2-carboxylic acid and 190 mg of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide monohydrochloride were added in order to a pyridine (2 ml) solution of 181 mg of t-butyl 2-(4-amino-2-fluoro-phenyl)-pyrrolidine-1-carboxylate, and the reaction liquid was stirred at room temperature for 3 hours. The reaction liquid was diluted with chloroform, washed with water and saturated saline, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and 2 ml of 4 N hydrochloric acid-dioxane solution was added to 300 mg of the resulting residue, and the reaction liquid was stirred at room temperature for 1 hour. The reaction liquid was diluted with chloroform, and made basic with aqueous saturated sodium bicarbonate solution added thereto, and the organic layer was washed with saturated saline and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and 0.020 ml of acetic anhydride was added to a pyridine (1 ml) solution of the resulting residue, and the reaction liquid was stirred at room temperature for 20 minutes. The reaction liquid was diluted with chloroform, washed with water and saturated saline in order, and dried with anhydrous magnesium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=50/1) to obtain the entitled compound as a yellow solid.

後処理

  1. customthe reaction liquid
  2. customThe reaction liquid
  3. washwashed with water and saturated saline
  4. dry with materialdried with anhydrous magnesium sulfate
  5. customThe solvent was evaporated away under reduced pressure, and 2 ml of 4 N hydrochloric acid-dioxane solution
  6. additionwas added to 300 mg of the resulting residue
  7. customthe reaction liquid
  8. stirringwas stirred at room temperature for 1 hour
  9. customThe reaction liquid
  10. additionadded
  11. washthe organic layer was washed with saturated saline
  12. dry with materialdried with anhydrous magnesium sulfate
  13. customThe solvent was evaporated away under reduced pressure, and 0.020 ml of acetic anhydride
  14. additionwas added to a pyridine (1 ml) solution of the resulting residue
  15. customthe reaction liquid
  16. stirringwas stirred at room temperature for 20 minutes
  17. customThe reaction liquid
  18. washwashed with water and saturated saline in order
  19. dry with materialdried with anhydrous magnesium sulfate
  20. customThe solvent was evaporated away under reduced pressure
  21. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=50/1)

出典と根拠

ORDレコード
ord-0b7e429ae81b453c8d805025d655020c
出典データセット
uspto-grants-2010_06
特許番号
US07728025B2

関連ノート

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