ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Toluene → 5-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one

HRID 1754806
ノート
印刷プレビュー

反応式

HRID 1754806 の反応式
C1(C)C=CC(S(O)(=O)=O)=CC=1.[S:12]1[CH:20]2[C:15]([CH2:16][NH:17][CH2:18][CH2:19]2)=[CH:14][C:13]1=[O:21].Br[CH:23]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[F:35])[C:24]([CH:26]1[CH2:28][CH2:27]1)=[O:25].C1COCC1.C1(C)C=CC=CC=1>CN(C=O)C.C(OCC)(=O)C.O.C(#N)C>[CH:26]1([C:24](=[O:25])[CH:23]([N:17]2[CH2:18][CH2:19][CH:20]3[S:12][C:13](=[O:21])[CH:14]=[C:15]3[CH2:16]2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[F:35])[CH2:28][CH2:27]1
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 1140TolueneHCID 8028TetrahydrofuranHCID 234358712-Bromo-1-cyclopropyl-2-(2-fluorophenyl)ethanoneHCID 451083204-Methylbenzene-1-sulfonic acid--5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one (1/1)

生成物 1

HCID 114162775-[2-Cyclopropyl-1-(2-fluorophenyl)-2-oxoethyl]-5,6,7,7a-tetrahydrothieno[3,2-c]pyridin-2(4H)-one

試薬・触媒・溶媒 4

HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒
HCID 6342Acetonitrile溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

According to the process of the present invention the 5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridine-2-on p-toluenesulfonate (HA=PTSA) of the formula (II) and the 2-bromo-1-cyclopropyl-2-(2-fluorphenyl)-ethanon of the formula (III) are stirred in an organic solvent, (preferably in DMF, THF, toluene, acetonitrile) by adding 1-3 mole equivalent, preferably 2-2.5 mole equivalents of amine, at 20-50° C., preferably 20-30° C., for 1-3, preferably 1-2 hours. The reaction mixture is then divided between water and ethyl acetate and the organic phase is dried and evaporated. The residual product is dissolved in an organic solvent (preferably in DMF, THF, toluene, acetonitrile) without isolating the crystalline 5-[2-cyclopropyl-1-(2-fluorphenyl)-2-oxoethyl]-5,6,7,7a-tetrahydro-4H-thieno[3,2-c]pyridine-2-on of the formula (IV). Then 1-2 equivalent, preferably 1-1.5 equivalent of an amine and 1-3 equivalent, preferably 1-2 equivalent of acetic acid anhydride is added to the reaction mixture and it is further stirred at 20-50° C., preferably 20-30° C., for 1-3 hours, preferably 1-2 hours. The reaction mixture is then divided between water and ethylacetate and the organic phase is dried and evaporated. The remaining product is recrystallized from a suitable organic solvent (acetonitrile, diisopropylether, ethanol), from the mixture of an organic solvent and water or from mixture of suitable organic solvents (toluene-ethyl acetate, hexane-ethyl acetate).

後処理

  1. customat 20-50° C.
  2. custompreferably 20-30° C.
  3. customfor 1-3, preferably 1-2 hours
  4. customthe organic phase is dried
  5. customevaporated
  6. dissolutionThe residual product is dissolved in an organic solvent (preferably in DMF, THF, toluene, acetonitrile)

出典と根拠

ORDレコード
ord-f1bbe354259344c69f0c362bca3f7b05
出典データセット
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09169265B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート