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

HRID 572355ノート

反応式

HRID 572355 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]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][CH:25]=2)[CH2:6][C@@H:5]1[CH3:31])(=[O:3])[CH3:2].[CH3:32][N:33]([CH3:38])[CH2:34][CH2:35][CH2:36]O.C(Cl)CCl>CN(C=O)C.CN(C1C=CN=CC=1)C>[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][CH2:36][CH2:35][CH2:34][N:33]([CH3:38])[CH3:32])=[O:19])=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([Cl:30])=[CH:28][CH:29]=2)[CH2:6][C@@H:5]1[CH3:31])(=[O:3])[CH3:2]

参加物

6

反応物 3

HCID 111,2-DichloroethaneHCID 766463-(Dimethylamino)-1-propanolHCID 529122224-[(2s,4r)-1-Acetyl-4-[(4-Chlorophenyl)amino]-2-Methyl-1,2,3,4-Tetrahydroquinolin-6-Yl]benzoic Acid

生成物 1

HCID 709799363-(dimethylamino)propyl 4-((2S,4R)-1-acetyl-4-((4-chlorophenyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate収率 17%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 4-{(2S,4R)-1-acetyl-4-[(4-chlorophenyl)amino]-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl}benzoic acid (for a preparation see Intermediate 18) (250 mg, 0.575 mmol) in DMF (10 mL) were successively added 3-(dimethylamino)-1-propanol (71.2 mg, 0.690 mmol), EDC (220 mg, 1.150 mmol) and DMAP (7.0 mg, 0.057 mmol). The resulting mixture was stirred at room temperature overnight, then concentrated in vacuo, dissolved in a 1:1 MeOH/DMSO mixture and 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-((4-chlorophenyl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)benzoate (41 mg, 17%) as a viscous colourless oil. LCMS (Formate, 2 min), Rt=0.94 min, MH+=520.

後処理

  1. concentrationconcentrated in vacuo
  2. dissolutiondissolved in a 1:1 MeOH/DMSO mixture
  3. custompurified by MDAP (HpH)
  4. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-42be5e8a0df54c5ba528983a7d234f9c
出典データセット
uspto-grants-2015_05
特許番号
US09029395B2

反応ノート

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