Potassium Carbonate → ethyl (2E)-3-(5-chloro-6-{[(3R)-1-(3-methylbenzyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylate

HRID 2376125노트

반응식

HRID 2376125 반응식
[Cl:1][C:2]1[CH:3]=[C:4](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:13][CH2:12][NH:11][CH2:10]1.[C:21]1([CH3:29])[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]=O)[CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4](/[CH:14]=[CH:15]/[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH:5]=[N:6][C:7]=1[NH:8][C@@H:9]1[CH2:13][CH2:12][N:11]([CH2:29][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=2)[CH2:10]1

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 121053-MethylbenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86603633ethyl (2E)-3-{5-chloro-6-[(3R)-3-pyrrolidinylamino]-3-pyridinyl}acrylate

생성물 1

HCID 86603735ethyl (2E)-3-(5-chloro-6-{[(3R)-1-(3-methylbenzyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylate수율 83.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
27.5 °C

실험 절차

A mixture of ethyl (2E)-3-{5-chloro-6-[(3R)-3-pyrrolidinylamino]-3-pyridinyl}acrylate (0.73 g), m-tolualdehyde (356 mg) and sodium triacetoxyborohydride (1.57 g) in CH2Cl2 (30 ml) was stirred at 25-30° C. for 15 hours. The 10% K2CO3 solution (20 ml) was added to a reaction mixture and resultant mixture was 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 AcOEt-MeOH (97:3). The eluted fractions containing the desired product were collected and evaporated in vacuo to give ethyl (2E)-3-(5-chloro-6-{[(3R)-1-(3-methylbenzyl)-3-pyrrolidinyl]amino}-3-pyridinyl)acrylate (820 mg).

후처리

  1. stirringwas stirred 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 AcOEt-MeOH (97:3)
  8. additionThe eluted fractions containing the desired product
  9. customwere collected
  10. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-b7e9da9ffaae4821bab60a4087dcafe4
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07465731B2

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