Hydrochloric Acid → 6-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-9-hydroxy-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

HRID 2169254노트

반응식

HRID 2169254 반응식
C([O:8][C:9]1[C:14](=[O:15])[N:13]=[C:12]([CH2:16][C:17]2([C:22]3[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:23]=3[Cl:29])[CH2:21][CH2:20][CH2:19][CH2:18]2)[N:11]2[CH2:30][CH2:31][N:32]([CH:35]([CH3:37])[CH3:36])[C:33](=[O:34])[C:10]=12)C1C=CC=CC=1.Cl.C(OCC)(=O)C>CO>[Cl:29][C:23]1[CH:24]=[CH:25][C:26]([Cl:28])=[CH:27][C:22]=1[C:17]1([CH2:16][C:12]2[N:11]3[CH2:30][CH2:31][N:32]([CH:35]([CH3:37])[CH3:36])[C:33](=[O:34])[C:10]3=[C:9]([OH:8])[C:14](=[O:15])[N:13]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 867259049-benzyloxy-6-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione

생성물 1

HCID 867259056-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-9-hydroxy-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione수율 11.34%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

To a stirred solution of 9-benzyloxy-6-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (208) (500 mg, 0.93 mmol) in methanol (5.5 mL) was added concentrated HCl (4 mL) and the mixture was stirred for 20 h. Silica thin layer chromatography was performed (100% ethyl acetate, Rf=0.3). Methanol was removed, water was added, the mixture was basified (pH˜8) with solid NaHCO3, extracted with ethyl acetate (3×20 mL), and the organic part was dried and concentrated. The crude product was purified by preparative HPLC purification to get 6-[1-(2,5-dichlorophenyl)-cyclopentylmethyl]-9-hydroxy-2-isopropyl-3,4-dihydro-2H-pyrazino[1,2-c]pyrimidine-1,8-dione (209) (32 mg, 11.34%) as a light brown solid.

후처리

  1. customMethanol was removed
  2. additionwater was added
  3. extractionextracted with ethyl acetate (3×20 mL)
  4. customthe organic part was dried
  5. concentrationconcentrated
  6. customThe crude product was purified by preparative HPLC purification

출처 및 근거

ORD 기록
ord-f47f4861811d4552942d62435e88770a
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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