Oxalyl chloride → HCID 9880843、化合物

HRID 352419ノート

反応式

HRID 352419 の反応式
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=O)=[CH:10][CH:9]=2)[CH:5]=[CH:6][CH:7]=1.C(Cl)(=O)C(Cl)=O.[NH:24]1[C:28]2[CH2:29][CH2:30][CH2:31][C:27]=2[C:26]([NH2:32])=[N:25]1>O1CCCC1.CN(C)C=O>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([CH2:14][C:15]([NH:32][C:26]3[C:27]4[CH2:31][CH2:30][CH2:29][C:28]=4[NH:24][N:25]=3)=[O:17])=[CH:12][CH:13]=2)[CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 65578Oxalyl chlorideHCID 1393660(3'-Fluoro[1,1'-biphenyl]-4-yl)acetic acidHCID 227120592,4,5,6-Tetrahydrocyclopenta[c]pyrazol-3-amine

生成物 1

HCID 9880843HCID 9880843、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

230 mg of 2-(3′-fluoro-biphenyl-4-yl)-acetic acid is dissolved in 5 ml of tetrahydrofuran, mixed with 0.11 ml of oxalyl chloride and one drop of dimethylformamide, and stirred for 2 hours at room temperature. 62 mg of 1,4,5,6-tetrahydro-cyclopentapyrazol-3-yl-amine is added to this solution. The mixture is stirred for 12 hours at room temperature and then concentrated by evaporation. The residue is extracted with ethyl acetate. The extract is washed with sodium bicarbonate solution and water, dried on magnesium sulfate and concentrated by evaporation. The brown residue is dissolved in 5 ml of methanol and mixed with 0.1 ml of a 30% sodium methylate solution. It is stirred for 4 hours at room temperature and then concentrated by evaporation. The residue is extracted with ethyl acetate. The extract is washed with sodium bicarbonate solution and sodium chloride solution, dried on magnesium sulfate and concentrated by evaporation. A yellow, resinous oil is obtained that is purified by HPLC. 2-(3′-Fluoro-biphenyl-4-yl)-N-(1,4,5,6-tetrahydro-cyclopentapyrazol-3-yl)-acetamide with a melting point of 180-181° C. is obtained.

後処理

  1. stirringThe mixture is stirred for 12 hours at room temperature
  2. concentrationconcentrated by evaporation
  3. extractionThe residue is extracted with ethyl acetate
  4. washThe extract is washed with sodium bicarbonate solution and water
  5. customdried on magnesium sulfate
  6. concentrationconcentrated by evaporation
  7. dissolutionThe brown residue is dissolved in 5 ml of methanol
  8. additionmixed with 0.1 ml of a 30% sodium methylate solution
  9. stirringIt is stirred for 4 hours at room temperature
  10. concentrationconcentrated by evaporation
  11. extractionThe residue is extracted with ethyl acetate
  12. washThe extract is washed with sodium bicarbonate solution and sodium chloride solution
  13. customdried on magnesium sulfate
  14. concentrationconcentrated by evaporation
  15. customA yellow, resinous oil is obtained
  16. customthat is purified by HPLC

出典と根拠

ORDレコード
ord-87d85bfe71ed464f99d0d5f8ee2c90b3
出典データセット
uspto-grants-2004_06
特許番号
US06747046B2

反応ノート

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