1,2-Dichloroethane → Tert-butyl 4-(2-{(cyclohexylcarbonyl) [(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]amino}-1-phenylethyl)piperidine-1-carboxylate

HRID 1943027노트

반응식

HRID 1943027 반응식
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[C:4]([CH2:12][NH:13][CH2:14][CH:15]([CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:3]1=[O:35].C(Cl)CCl.C1C=NC2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C.[CH:59]1([C:65](O)=[O:66])[CH2:64][CH2:63][CH2:62][CH2:61][CH2:60]1>C(Cl)Cl>[CH:59]1([C:65]([N:13]([CH2:12][C:4]2[C:3](=[O:35])[N:2]([CH3:1])[C:11]3[C:6]([CH:5]=2)=[CH:7][CH:8]=[CH:9][CH:10]=3)[CH2:14][CH:15]([CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[CH2:24][CH2:23]2)[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[O:66])[CH2:64][CH2:63][CH2:62][CH2:61][CH2:60]1

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 7413Cyclohexanecarboxylic acidHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 58415941Tert-butyl 4-(2-{[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]amino}-1-phenylethyl)piperidine-1-carboxylate

생성물 1

HCID 58415912Tert-butyl 4-(2-{(cyclohexylcarbonyl) [(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]amino}-1-phenylethyl)piperidine-1-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

tert-butyl 4-(2-{[(1-methyl-2-oxo-1,2-dihydroquinolin-3-yl)methyl]amino}-1-phenylethyl)piperidine-1-carboxylate (1.61 g crude, 3.39 mmol), EDC (1.298 g, 6.77 mmol), HOAT (0.461 g, 3.39 mmol), DIEA (1.182 ml, 6.77 mmol), and cyclohexanecarboxylic acid (0.504 ml, 4.06 mmol) were combined in CH2Cl2 and the reaction stirred for 15 hours. The mixture was partitioned between CH2Cl2 and satd. bicarb, the aqueous portion extracted 3×CH2Cl2, and the organic portion dried (Na2SO4) then concentrated in vacuo. The resulting material was purified by silica gel chromatography on an Isco Companion. The desired fractions were combined and concentrated in vacuo. 1.63 g, 82% over two steps.

후처리

  1. customThe mixture was partitioned between CH2Cl2 and satd
  2. extractionbicarb, the aqueous portion extracted 3×CH2Cl2
  3. dry with materialthe organic portion dried (Na2SO4)
  4. concentrationthen concentrated in vacuo
  5. customThe resulting material was purified by silica gel chromatography on an Isco Companion
  6. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-dd00ba19f87b40e5b7bac85a36329e7d
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08389720B2

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