Diisopropylethylamine → (R)-1-(4-(6-benzyl-2-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazin-1-yl)ethanone

HRID 80780노트

반응식

HRID 80780 반응식
[CH2:1]([N:8]1[CH2:19][CH2:18][C:11]2[N:12]=[C:13]([Cl:17])[N:14]=[C:15](Cl)[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.[CH3:27][C@H:28]1[NH:33][CH2:32][CH2:31][N:30]([C:34](=[O:36])[CH3:35])[CH2:29]1.CCN(C(C)C)C(C)C>CC(O)C.CCOC(C)=O>[CH2:1]([N:8]1[CH2:19][CH2:18][C:11]2[N:12]=[C:13]([Cl:17])[N:14]=[C:15]([N:33]3[CH2:32][CH2:31][N:30]([C:34](=[O:36])[CH3:35])[CH2:29][C@H:28]3[CH3:27])[C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 81531DiisopropylethylamineHCID 378190156-Benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido(4,3-d)pyrimidineHCID 86690248(R)-1-(3-methylpiperazin-1-yl)ethanone 2,2,2-trifluoroacetate

생성물 1

HCID 86690255(R)-1-(4-(6-benzyl-2-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazin-1-yl)ethanone

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

A mixture of 6-benzyl-2,4-dichloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (0.655 g, 1.89 mmol), (R)-1-(3-methylpiperazin-1-yl)ethanone 2,2,2-trifluoroacetate (1 g, 2.84 mmol) and DIEA (2.65 mL, 15.2 mmol) in i-PrOH (25 mL) was heated to 80° C. for 48 h. The reaction mixture was then diluted with EtOAc, and washed successively with sat aq NaHCO3 and brine. The organic layer was then dried over Na2SO4, filtered and concentrated. The resulting residue was diluted with DCM and filtered to remove solid. The filtrate was concentrated and purified by FCC (0-5% MeOH in DCM) to provide (R)-1-(4-(6-benzyl-2-chloro-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazin-1-yl)ethanone. MS (ESI+) m/z 400.3 (M+H)+.

후처리

  1. washwashed successively with sat aq NaHCO3 and brine
  2. dry with materialThe organic layer was then dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. additionThe resulting residue was diluted with DCM
  6. filtrationfiltered
  7. customto remove solid
  8. concentrationThe filtrate was concentrated
  9. custompurified by FCC (0-5% MeOH in DCM)

출처 및 근거

ORD 기록
ord-2411be6a1dd2413d9b652ef68b704825
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846656B2

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