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

HRID 2376135
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HRID 2376135 반응식
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
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참가 물질

7

반응물 4

HCID 8452CyclopentanoneHCID 11430Potassium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 86603743ethyl (2Z)-3-{5-chloro-6-[(3R)-3-pyrrolidinylamino]-3-pyridinyl}-2-fluoroacrylate dihydrochloride

생성물 1

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

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8471Triethylamine용매

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온도
27.5 °C

실험 절차

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 (20 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).

후처리

  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

출처 및 근거

ORD 기록
ord-6c8ef3e9064f497795bc139b8d4195ea
출처 데이터셋
uspto-grants-2008_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07465731B2

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