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Triethylamine → 1-[3-(2-Phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-ethylpiperidine

HRID 1029422
ノート
印刷プレビュー

反応式

HRID 1029422 の反応式
ClC(OCC(C)C)=O.[C:9]1([C:15]2[C:23]([CH:24]=[CH:25][C:26](O)=[O:27])=[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][N:17]3[N:16]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C.[CH2:36]([CH:38]1[CH2:43][CH2:42][CH2:41][CH2:40][NH:39]1)[CH3:37]>C(Cl)Cl.O1CCCC1>[C:9]1([C:15]2[C:23]([CH:24]=[CH:25][C:26]([N:39]3[CH2:40][CH2:41][CH2:42][CH2:43][CH:38]3[CH2:36][CH3:37])=[O:27])=[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][N:17]3[N:16]=2)[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 942052-EthylpiperidineHCID 53923255HCID 53923255、化合物

生成物 1

HCID 540385431-[3-(2-Phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-ethylpiperidine

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒
HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

Isobutyl chloroformate (1.04 g) was added dropwise to a mixture of 3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acrylic acid (trans isomer) (2.0 g) and triethylamine (0.766 g) in methylene chloride (40 ml) and tetrahydrofuran (10 ml) at -20° C. with stirring. After being stirred at the same temperature for 30 minutes, a solution of 2-ethylpiperidine (0.942 g) in tetrahydrofuran (10 ml) was added thereto dropwise at -20° C. and the mixture was stirred at -20° C. to 10° C. for 2 hours. The mixture was warmed to room temperature and evaporated in vacuo. A saturated sodium bicarbonate solution was added to the residue and extracted twice with chloroform (50 ml ). The combined extract was washed with saturated brine (50 ml), dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel (40 g) with chloroform as an eluent. The fractions containing the object compound were combined and evaporated in vacuo t give 1-[3-(2-phenylpyrazolo[1,5-a]pyridin-3-yl)acryloyl]-2-ethylpiperidine (trans isomer](1.30 g) as an oil.

後処理

  1. stirringAfter being stirred at the same temperature for 30 minutes
  2. stirringdropwise at -20° C. and the mixture was stirred at -20° C. to 10° C. for 2 hours
  3. customevaporated in vacuo
  4. additionA saturated sodium bicarbonate solution was added to the residue
  5. extractionextracted twice with chloroform (50 ml )
  6. extractionThe combined extract
  7. washwas washed with saturated brine (50 ml)
  8. dry with materialdried over magnesium sulfate
  9. customevaporated in vacuo
  10. customThe residue was chromatographed on silica gel (40 g) with chloroform as an eluent
  11. additionThe fractions containing the object compound
  12. customevaporated in vacuo

出典と根拠

ORDレコード
ord-3772d127d91d4ee19a37df5bdc4d51e9
出典データセット
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05102869

反応ノート

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