(R)-2-(1-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-imidazol-4-yl)acetonitrile → (R)-2-(4-(2-aminoethyl)-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one

HRID 44839

반응식

HRID 44839 반응식
[CH:1]1([N:6]2[C:15]3[N:14]=[C:13]([N:16]4[CH:20]=[C:19]([CH2:21][C:22]#[N:23])[N:18]=[CH:17]4)[N:12]=[CH:11][C:10]=3[N:9]([CH3:24])[C:8](=[O:25])[C@H:7]2[CH2:26][CH3:27])[CH2:5][CH2:4][CH2:3][CH2:2]1>CCOC(C)=O.O=[Pt]=O>[NH2:23][CH2:22][CH2:21][C:19]1[N:18]=[CH:17][N:16]([C:13]2[N:12]=[CH:11][C:10]3[N:9]([CH3:24])[C:8](=[O:25])[C@@H:7]([CH2:26][CH3:27])[N:6]([CH:1]4[CH2:5][CH2:4][CH2:3][CH2:2]4)[C:15]=3[N:14]=2)[CH:20]=1

참가 물질

4

반응물 1

HCID 58405740(R)-2-(1-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-imidazol-4-yl)acetonitrile

생성물 1

HCID 58405893(R)-2-(4-(2-aminoethyl)-1H-imidazol-1-yl)-8-cyclopentyl-7-ethyl-5-methyl-7,8-dihydropteridin-6(5H)-one수율 42.2%

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 8857Ethyl Acetate용매

실험 절차

(R)-2-(1-(8-cyclopentyl-7-ethyl-5-methyl-6-oxo-5,6,7,8-tetrahydropteridin-2-yl)-1H-imidazol-4-yl)acetonitrile (Example 35, 0.08 g, 0.218 mmol) and PtO2 (40 mg) were suspended in 2 mL of EtOAc and the resulting mixture was stirred under an atmosphere of hydrogen (1 atm, balloon) for 18 h. The resulting solution was filtered through Celite, concentrated, then purified by preparative HPLC to give the title compound (34 mg). LCMS: 370.1 m/z (M+H)+; ret. Time: 4.09 (Analytical Method C).

후처리

  1. filtrationThe resulting solution was filtered through Celite
  2. concentrationconcentrated
  3. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-375633b2085a4bb3a7a0ebd80fb12d18
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541418B2

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