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Cyclopentanone → ethyl (2Z)-3-(5-chloro-6-([(3R)-1-cyclopentyl-3-pyrrolidinyl]amino)-3-pyridinyl)-2-fluoroacrylate

HRID 226439
ノート
印刷プレビュー

反応式

HRID 226439 の反応式
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6](/[CH:16]=[C:17](\[F:23])/[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:7]=[N:8][C:9]=1[NH:10][C@@H:11]1[CH2:15][CH2:14][NH:13][CH2:12]1.[C:24]1(=O)[CH2:28][CH2:27][CH2:26][CH2:25]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[K+].[K+]>C(Cl)(Cl)Cl.CCN(CC)CC>[Cl:3][C:4]1[CH:5]=[C:6](/[CH:16]=[C:17](\[F:23])/[C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:7]=[N:8][C:9]=1[NH:10][C@@H:11]1[CH2:15][CH2:14][N:13]([CH:24]2[CH2:28][CH2:27][CH2:26][CH2:25]2)[CH2:12]1
参加物反応条件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 8452CyclopentanoneHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86603743ethyl (2Z)-3-{5-chloro-6-[(3R)-3-pyrrolidinylamino]-3-pyridinyl}-2-fluoroacrylate dihydrochloride

生成物 1

HCID 86603745ethyl (2Z)-3-(5-chloro-6-([(3R)-1-cyclopentyl-3-pyrrolidinyl]amino)-3-pyridinyl)-2-fluoroacrylate収率 99.9%

試薬・触媒・溶媒 2

HCID 6212Chloroform溶媒HCID 8471Triethylamine溶媒

反応条件

温度
27.5 °C

実験手順

A mixture of ethyl (2Z)-3-{5-chloro-6-[(3R)-3-pyrrolidinylamino]-3-pyridinyl}-2-fluoroacrylate dihydrochloride (720 mg), cyclopentanone (188 mg), sodium triacetoxyborohydride (1.18 g) and Et3N (0.52 ml) in CHCl3 (20 ml) was stirred at 25-30° C. for 15 hours. The 10% K2CO3 solution (2 ml) was added to a reaction mixture and stirred at ambient temperature for 30 minutes and extracted with CH2Cl2 and washed with brine and dried over MgSO4. The solvent was evaporated in vacuo and the residue was chromatographed on silicagel eluting with CHCl3-MeOH (96:4). The eluted fractions containing the desired product were collected and evaporated in vacuo to give ethyl (2Z)-3-(5-chloro-6-([(3R)-1-cyclopentyl-3-pyrrolidinyl]amino)-3-pyridinyl)-2-fluoroacrylate (710 mg).

後処理

  1. stirringstirred at ambient temperature for 30 minutes
  2. extractionextracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was evaporated in vacuo
  6. customthe residue was chromatographed on silicagel
  7. washeluting with CHCl3-MeOH (96:4)
  8. additionThe eluted fractions containing the desired product
  9. customwere collected
  10. customevaporated in vacuo

出典と根拠

ORDレコード
ord-20966383d321434b86b5035f2eb83624
出典データセット
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07557127B2

反応ノート

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