Diisopropylethylamine → Methyl 5-(2,6-dimethoxyphenyl)-5-((quinolin-3-ylmethyl)amino)pentanoate

HRID 594384

반응식

HRID 594384 반응식
[NH2:1][CH:2]([C:10]1[C:15]([O:16][CH3:17])=[CH:14][CH:13]=[CH:12][C:11]=1[O:18][CH3:19])[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].CCN(C(C)C)C(C)C.[N:29]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:32]=[C:31]([CH:39]=O)[CH:30]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.C(Cl)Cl>[CH3:19][O:18][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([O:16][CH3:17])[C:10]=1[CH:2]([NH:1][CH2:39][C:31]1[CH:30]=[N:29][C:38]2[C:33]([CH:32]=1)=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:3][CH2:4][CH2:5][C:6]([O:8][CH3:9])=[O:7]

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 836413-QuinolinecarboxaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 69082713Methyl 5-amino-5-(2,6-dimethoxyphenyl)pentanoate

생성물 1

HCID 69082480Methyl 5-(2,6-dimethoxyphenyl)-5-((quinolin-3-ylmethyl)amino)pentanoate

시약·촉매·용매 2

HCID 111,2-Dichloroethane용매HCID 6344Dichloromethane용매

실험 절차

A solution of the chlorhydrate salt of methyl 5-amino-5-(2,6-dimethoxyphenyl)pentanoate (1.177 g; 3.87 mmol; 1.0 equiv.) in anh. DCE (24 ml) was treated successively with DIPEA (1.35 ml; 7.75 mmol; 2.0 equiv.), quinoline-3-carbaldehyde (609 mg; 3.87 mmol; 1.0 equiv.), and NaBH(OAc)3 (1.150 g; 5.42 mmol; 1.4 equiv.). The resulting beige heterogeneous mixture was further stirred at rt, under nitrogen, for 2 h 45 min. DCM (50 ml) and a solution of aq. sat. NaHCO3 (35 ml) were then added. The organic layer was further washed with a solution of aq. sat. NaHCO3 (35 ml) and with brine (35 ml). The resulting yellow organic layer was then dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=10/1) afforded methyl 5-(2,6-dimethoxyphenyl)-5-((quinolin-3-ylmethyl)amino)-pentanoate as a yellow oil. LC-MS (conditions B): tR=0.66 min.; [M+H]+: 409.35 g/mol.

후처리

  1. washThe organic layer was further washed with a solution of aq. sat. NaHCO3 (35 ml) and with brine (35 ml)
  2. dry with materialThe resulting yellow organic layer was then dried over anh. MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure
  5. customPurification by FC (DCM/MeOH=10/1)

출처 및 근거

ORD 기록
ord-090ab0b42baf47889d987d836ecc4bdd
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242970B2

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