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 80780ノート

反応式

HRID 80780 の反応式
[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

参加物

6

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-2411be6a1dd2413d9b652ef68b704825
出典データセット
uspto-grants-2014_09
特許番号
US08846656B2

反応ノート

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