Methylamine → Tert-butyl {[2-isobutyl-6-[2-(methylamino)-2-oxoethoxy]-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate

HRID 1986434노트

반응식

HRID 1986434 반응식
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:11]([CH2:32][CH:33]([CH3:35])[CH3:34])=[N:12][C:13]2[C:18]([C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=[CH:17][C:16]([O:27][CH2:28][C:29]([OH:31])=O)=[CH:15][CH:14]=2)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH2:37]([N:39]=C=NCCCN(C)C)C.ON1C2C=CC=CC=2N=N1.CN>CN(C)C=O.O1CCCC1.O>[CH2:32]([C:11]1[C:10]([CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[C:19]([C:20]2[CH:21]=[CH:22][C:23]([CH3:26])=[CH:24][CH:25]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([O:27][CH2:28][C:29]([NH:39][CH3:37])=[O:31])[CH:17]=2)[N:12]=1)[CH:33]([CH3:34])[CH3:35]

참가 물질

8

반응물 4

HCID 6329MethylamineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 68829615{[3-{[(Tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}acetic acid

생성물 1

HCID 86605629Tert-butyl {[2-isobutyl-6-[2-(methylamino)-2-oxoethoxy]-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate수율 55%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of {[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]oxy}acetic acid (0.48 g, 1.0 mmol) in N,N-dimethylformamide (10 ml) were added 1-ethyl-3(3-dimethylaminopropyl)carbodiimide hydrochloride (0.23 g, 1.2 mmol), 1-hydroxy-1H-benzotriazole (0.16 g, 1.2 mmol) and 1.0 M solution of methylamine in tetrahydrofuran (2 ml) and the mixture was stirred at room temperature for 12 hrs. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The extract was washed with 1N hydrochloric acid and saturated brine, and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give tert-butyl {[2-isobutyl-6-[2-(methylamino)-2-oxoethoxy]-4-(4-methylphenyl)quinolin-3-yl]methyl}carbamate (0.27 g, yield 55%) as pale-yellow crystals.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with 1N hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-b451df036ab04ee6bb8bc3a1c1b25c0c
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07547710B2

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