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3-(Dimethylamino)-1-propanol → 3-(dimethylamino)propyl 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate

HRID 572358
ノート
印刷プレビュー

反応式

HRID 572358 の反応式
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:23][C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25])[CH2:6][C@@H:5]1[CH3:30])(=[O:3])[CH3:2].[CH3:31][N:32]([CH3:37])[CH2:33][CH2:34][CH2:35]O.Cl.C(N=C=NCCCN(C)C)C>CN(C=O)C.CN(C)C1C=CN=CC=1.O.CCOC(C)=O>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([O:20][CH2:35][CH2:34][CH2:33][N:32]([CH3:37])[CH3:31])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:23][C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25])[CH2:6][C@@H:5]1[CH3:30])(=[O:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 3

HCID 766463-(Dimethylamino)-1-propanolHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 67193625HCID 67193625、化合物

生成物 1

HCID 709803773-(dimethylamino)propyl 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate収率 15%

試薬・触媒・溶媒 4

HCID 14284
4-(Dimethylamino)pyridine
触媒
HCID 962Water溶媒
HCID 6228Dimethylformamide溶媒
HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoic acid (for a preparation see Intermediate 21) (164 mg, 0.400 mmol) and 3-(dimethylamino)propan-1-ol (206 mg, 1.998 mmol) in DMF (3 mL) were added N1-((ethylimino)methylene)-N3,N3-dimethylpropane-1,3-diamine hydrochloride (153 mg, 0.799 mmol) and N,N-dimethylpyridin-4-amine (4.88 mg, 0.040 mmol). The resulting mixture was stirred at room temperature for 2 h, the reaction mixture was diluted with water and EtOAc was added. The layers were separated and the aqueous phase was extracted with EtOAc (×3). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The residue was dissolved in a 1:1 MeOH/DMSO mixture and was purified by MDAP (HpH). The appropriate fractions were combined and concentrated under reduced pressure to give 3-(dimethylamino)propyl 4-((2S,4R)-1-acetyl-4-((isopropoxycarbonyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (29.3 mg, 15%) as a viscous colourless oil. LCMS (Formate, 2 min), Rt=0.75 min, MH+=476.

後処理

  1. additionwas added
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted with EtOAc (×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. dissolutionThe residue was dissolved in a 1:1 MeOH/DMSO mixture
  9. customwas purified by MDAP (HpH)
  10. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-5db786fe29554336bcef3ddbdcc517cf
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09029395B2

反応ノート

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