Dimethyl Sulfoxide → (1S,3R)-3-(5'-chloro-6-(3-fluorobenzylamino)-2,4'-bipyridin-2'-yl-amino)cyclopentanecarbaldehyde

HRID 1623375노트

반응식

HRID 1623375 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([NH:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=3)[N:27]=2)=[CH:14][C:15]([NH:18][C@@H:19]2[CH2:23][CH2:22][C@H:21]([CH2:24][OH:25])[CH2:20]2)=[N:16][CH:17]=1>C(Cl)Cl.CCOC(C)=O>[Cl:11][C:12]1[C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([NH:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[C:36]([F:40])[CH:35]=3)[N:27]=2)=[CH:14][C:15]([NH:18][C@@H:19]2[CH2:23][CH2:22][C@H:21]([CH:24]=[O:25])[CH2:20]2)=[N:16][CH:17]=1

참가 물질

6

반응물 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 66937105((1S,3R)-3-(5'-chloro-6-(3-fluorobenzylamino)-2,4'-bipyridin-2'-yl-amino)cyclopentyl)methanol

생성물 1

HCID 86689274(1S,3R)-3-(5'-chloro-6-(3-fluorobenzylamino)-2,4'-bipyridin-2'-yl-amino)cyclopentanecarbaldehyde

시약·촉매·용매 2

HCID 6344Dichloromethane용매4회HCID 8857Ethyl Acetate용매

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온도
-78 °C

실험 절차

In a flame-dried argon purged 20 mL conical flask, oxalyl chloride (0.025 ml, 0.281 mmol) was dissolved in DCM (0.5 ml) and cooled to −78° C. under argon. DMSO (0.030 ml, 0.422 mmol) was dissolved in DCM (0.5 ml) and added dropwise to the previous solution (I don't see issues here). This was stirred for 30 min at −78° C. ((1S,3R)-3-(5′-chloro-6-(3-fluorobenzylamino)-2,4′-bipyridin-2′-yl-amino)cyclopentyl)methanol (60 mg, 0.141 mmol) was dissolved in DCM (0.5 ml) and added dropwise to the reaction mixture. The resulting mixture was stirred for 60 min at −78° C. TEA (0.078 ml, 0.562 mmol) was dissolved in DCM (0.5 ml) and added dropwise to the reaction mixture, after which the reaction mixture was allowed to stir and warm to ambient temp over 2 hr. The reaction mixture was diluted with EtOAc, washed with saturated NH4Cl (30 mL×3), H2O (30 mL), brine (30 mL), dried over Na2SO4 and reduced. The resulting residue was used without further purification. LCMS (m/z): 425.2 (MH+), retention time=0.72.

후처리

  1. customIn a flame-dried argon purged 20 mL conical flask
  2. additionadded dropwise to the previous solution (I
  3. additionadded dropwise to the reaction mixture
  4. additionadded dropwise to the reaction mixture
  5. stirringto stir
  6. temperaturewarm to ambient temp over 2 hr
  7. washwashed with saturated NH4Cl (30 mL×3), H2O (30 mL), brine (30 mL)
  8. dry with materialdried over Na2SO4
  9. customThe resulting residue was used without further purification

출처 및 근거

ORD 기록
ord-5a9ad26113df494bb8a30aa9558e557c
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08778951B2

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