Water → 6-(2,6-Dimethoxyphenyl)-1-(quinolin-3-ylmethyl)piperidin-2-one

HRID 594386

반응식

HRID 594386 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][CH3:10])[C:4]=1[CH:11]([NH:18][CH2:19][C:20]1[CH:21]=[N:22][C:23]2[C:28]([CH:29]=1)=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.O>CN(C=O)C.CCOCC>[CH3:10][O:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[CH:11]1[N:18]([CH2:19][C:20]2[CH:21]=[N:22][C:23]3[C:28]([CH:29]=2)=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:15](=[O:17])[CH2:14][CH2:13][CH2:12]1

참가 물질

7

반응물 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 690835275-(2,6-Dimethoxyphenyl)-5-((quinolin-3-ylmethyl)amino)pentanoic acid

생성물 1

HCID 690841526-(2,6-Dimethoxyphenyl)-1-(quinolin-3-ylmethyl)piperidin-2-one

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

A yellow solution of 5-(2,6-dimethoxyphenyl)-5-((quinolin-3-ylmethyl)amino)pentanoic acid (1.074 g; 2.72 mmol; 1.0 equiv.) in anh. DMF (50 ml) was treated successively with HATU (1.294 g; 3.40 mmol; 1.25 equiv.) and with DIPEA (0.59 ml; 3.40 mmol; 1.25 equiv.). The resulting orange solution was stirred at rt, under nitrogen, for 2 h45. Water (100 ml) and Et2O (100 ml) were then added, and the separated aq. layer was further extracted with Et2O (3×100 ml). The mixed organic layers were washed with water (15 ml) and with brine (15 ml), dried over anh. MgSO4, filtered, and concentrated to dryness under reduced pressure. Purification by FC (DCM/MeOH=20/1) afforded 6-(2,6-dimethoxyphenyl)-1-(quinolin-3-ylmethyl)piperidin-2-one as a beige solid. LC-MS (conditions B): tR=0.68 min.; [M+H]+: 377.36 g/mol.

후처리

  1. extractionthe separated aq. layer was further extracted with Et2O (3×100 ml)
  2. washThe mixed organic layers were washed with water (15 ml) and with brine (15 ml)
  3. dry with materialdried over anh. MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customPurification by FC (DCM/MeOH=20/1)

출처 및 근거

ORD 기록
ord-29b83cfe6d604eb1ac04533905f7b07a
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09242970B2

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