Chloroacetaldehyde → (R)-3-chloro-5-cyclopentyl-6-ethyl-5,6-dihydroimidazo[1,2-f]pteridine

HRID 562509노트

반응식

HRID 562509 반응식
[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]=[C:7]([NH2:12])[C@@H:6]([CH2:13][CH3:14])[N:5]([CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:4]=2[N:3]=1.Cl[CH2:21][CH:22]=O.C([O-])(O)=O.[Na+].CCOC(C)=O>CO>[Cl:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]3[CH:21]=[CH:22][N:12]=[C:7]3[C@@H:6]([CH2:13][CH3:14])[N:5]([CH:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)[C:4]=2[N:3]=1

참가 물질

6

반응물 4

HCID 33Chloroacetaldehyde2회HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 59389593(R)-2-chloro-8-cyclopentyl-7-ethyl-7,8-dihydropteridin-6-amine

생성물 1

HCID 59389590(R)-3-chloro-5-cyclopentyl-6-ethyl-5,6-dihydroimidazo[1,2-f]pteridine

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
68 °C

실험 절차

(R)-2-chloro-8-cyclopentyl-7-ethyl-7,8-dihydropteridin-6-amine (177 mg, 0.64 mmol) in MeOH (1.5 mL) treated with 50% aqueous chloroacetaldehyde (131 μL, 1.3 Eq.) and the reaction mixture heated to reflux for 6 hours. A further portion of 50% aq. chloroacetaldehyde (400 μL, 3.0 Eq.) was added, and the reaction mixture heated to 68° C. overnight. NaHCO3 (aq. sat.) and EtOAc was added, and the aqueous was further extracted with EtOAc. The combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo.

후처리

  1. temperaturethe reaction mixture heated
  2. temperatureto reflux for 6 hours
  3. extractionthe aqueous was further extracted with EtOAc
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-e4dffabe574c49b588f5c33090d51fbf
출처 데이터셋
uspto-grants-2011_11
특허 번호
US08067417B2

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