Triethylamine → 3-(Methylsulfonylamino-methyl)-2-phenyl-quinoline-4-carboxylic acid ((S)-1-phenyl-propyl)-amide

HRID 655908노트

반응식

HRID 655908 반응식
[NH2:1][CH2:2][C:3]1[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([NH:15][C@H:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:17][CH3:18])=[O:14])=[CH:10][CH:9]=[CH:8][CH:7]=2.C(N(CC)CC)C.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(Cl)Cl>[C:19]1([C@@H:16]([NH:15][C:13]([C:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]=[C:4]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:3]=2[CH2:2][NH:1][S:39]([CH3:38])(=[O:41])=[O:40])=[O:14])[CH2:17][CH3:18])[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 578935693-(aminomethyl)-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide

생성물 1

HCID 236493293-(Methylsulfonylamino-methyl)-2-phenyl-quinoline-4-carboxylic acid ((S)-1-phenyl-propyl)-amide수율 42%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 3-(aminomethyl)-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide (2e) (197 mg, 0.5 mmol) in DCM (30 ml) was added triethylamine (140 μL, 1.0 mmol) under N2. Upon cooling with ice-water bath, methanesulfonyl chloride (39 μL, 0.51 mmol) was added dropwise and the reaction mixture stirred at RT for additional 2 h. Washed the mixture with brine (10 mL) and the organic phase was separated and dried over sodium sulfate and then concentrated in vacuo. The residue was purified by chromatography eluting with 15-25% ethyl acetate/hexane to give the title compound (79 mg, 42%) as a solid. 1H NMR (300 MHz, CDCl3) δ 0.94 (t, 3H), 1.95 (m, 2H), 2.99 (s, 3H), 4.88 (s, 2H), 5.25 (q, 1H), 6.66 (b, 2H), 7.30 (d, 2H), 7.34 (d, 2H), 7.39 (m, 1H), 7.78 (m, 2H), 7.84 (m, 2H), 8.08 (m, 1H), 8.30 (m, 2H), 8.20 (m, 2H). MS APCI, m/z=474 (M+1). LCMS: 2.16 min.

후처리

  1. temperatureUpon cooling with ice-water bath
  2. washWashed the mixture with brine (10 mL)
  3. customthe organic phase was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography
  7. washeluting with 15-25% ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-018f5798b4344b26bc44eaa5343fb97d
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08071621B2

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